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Fresh Pineapple Upside Down Cake Recipe

The upside down cake has survived many transformations. Originally cooked in a cast iron skillet over an open flame, the one-pan wonder grew in popularity with the introduction of canned tropical fruit in the early 1900s.
By the 1950s, yellow cake mix, pineapple rings and red candied cherries became the fashionable norm, and no dinner party was complete without the iconic dessert.
This updated Pineapple Upside Down Cake recipe uses fresh pineapple (Not sure how to cut a pineapple? Get our guide here!) slices arranged in a funky geometric design more fitting the current century and contains less saturated fat then the original. You can thank Martha Stewart for this lighter, yet still so incredible version of the forever-popular cake.

Fresh Pineapple Upside Down Cake Recipe


Picture of pineapple credit: richard-north, Flickr.


I usually use cooking spray, but for this cake I recommend brushing the pan and parchment with cooking oil.

I could only fit 12 slices in my 8 inch pan.

I could only fit 12 slices in my 8-inch pan.


It’s okay if your batter is not completely smooth.

Fresh Pineapple Upside Down Cake Recipe
Recipe type: Dessert
Cuisine: American
This Fresh Pineapple Upside Down Cake recipe is light and delicious!
  • ⅓ cup canola oil, plus a little for the pan
  • 1 cup packed light brown sugar, divided
  • 1 ripe firm pineapple, cut into 16 thin wedges
  • 1 cup all-purpose flour
  • ½ cup whole-wheat flour
  • 1 ½ teaspoons baking powder
  • ½ teaspoon salt
  • ¾ cup buttermilk
  • 2 large eggs
  • 1 teaspoon vanilla
  1. Preheat oven to 350 degrees. Brush an 8- or 9-inch square baking dish with cooking oil. Line with a strip of parchment paper, leaving and overhang on two sides. Brush paper with oil. Sprinkle bottom of pan with ¼ cup brown sugar.
  2. Trim pineapple slices if necessary and arrange in groups, alternating directions.
  3. In a medium bowl, whisk together flours, baking powder, baking soda and salt; set aside.
  4. In a large bowl, whisk together buttermilk, eggs, oil, vanilla and remaining ¾ cup sugar.
  5. Add flour mixture to the egg mixture and mix just until combined. Pour batter over pineapple.
  6. Tap pan firmly on counter to settle batter.
  7. Bake until a toothpick inserted in center of cakes comes out clean, 40 to 50 minutes, depending on size of pan. Cool 20 minutes in pan; invert onto a serving platter, peel and discard paper.

What’s your favorite fresh pineapple recipe? Do you love pineapple upside down cake, too? –Karen

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