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Pineapple Upside Down Cake

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best pineapple upside down cake recipe

There’s a reason the classics are, well,.. classic. They have stood the test of time and, in many cases, bring with them a sense of nostalgia when we make or eat them. Pineapple upside-down cake was a go-to recipe for my mom and was guaranteed to make an appearance at most family gatherings. 

I’ve made a few changes to mom’s recipe, but the basic idea remains the same. The cake to fruit ratio is perfect and the brown sugar makes a lovely, crunchy topping. I’ve added a bit of cardamom to enhance the flavor and used almond extract instead of vanilla. One thing I did not skip,.. maraschino cherries. I don’t use them often, but it just wouldn’t be pineapple upside-down cake without them.

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best pineapple upside down cake recipe

The ingredients:

  • 7-8 pineapple slices, from 1 can (reserve juice)
  • 6 tablespoons unsalted butter
  • ¾ cup light brown sugar
  • 13-15 maraschino cherries, without stems
  • 1½ cups flour
  • 2 teaspoons baking powder
  • ¼ teaspoon salt
  • 2 teaspoons ground cardamom
  • 6 tablespoons unsalted butter, at room temperature
  • 1 cup sugar
  • 2 eggs
  • 1 teaspoon almond extract
  • ½ teaspoon coconut extract
  • ½ cup pineapple juice
best pineapple upside down cake recipe

The method:

  1. Add 6 tablespoons butter to a non-stick skillet over medium heat to melt. When butter has melted stir in brown sugar to dissolve. Add pineapple slices and continue to cook for another 3-4 minutes, turning the slices after a minute or two. Remove from the heat to cool slightly.
  2. Preheat oven to 350˚F. Cut a circle from parchment paper to line a 9-inch cake pan ( we used a springform pan) with at least 2-inch sides. Lightly grease the pan and add the parchment paper to the bottom. 
  3. Add one full pineapple slice to the center of the cake pan. Cut the remaining pineapple slices in half. Fan the remaining pineapple pieces around the center pineapple circle. Place a maraschino cherry in the center of the full pineapple slice and in the inner curve of each of the pineapple slice halves. Pour the remaining butter/sugar mixture over the pineapple and cherries, taking care not to disturb their positions. Set aside.
  4. Sift the flour, baking powder, salt, and cardamom together. Set aside.
  5. Beat the butter on medium speed until light and creamy. Add sugar and beat for 2-3 more minutes until light and fluffy. Add eggs, one at a time, beating after each to fully incorporate. 
  6. Add half of the sifted, dry ingredients to the mixing bowl and beat until fully incorporated. Add the extracts and pineapple juice and beat until fully incorporated. Add the remaining dry ingredients and beat to fully combine.
  7. Add the batter to the cake pan, being careful to not disturb the placement of the fruit. Use an offset spatula or the back of a spoon to evenly distribute the batter. Bake the cake for 40-45 minutes or until golden brown. Check for doneness with a clean toothpick test.
  8. Allow the cake to cool for 10 minutes on a wire rack. Use a paring knife to make sure that the cake has pulled away from the sides. Place a plate over the cake pan and invert them together. Carefully remove the cake pan. Gently peel back the parchment paper and reposition any fruit that has moved or stuck to the parchment.
  9. Serve warm or at room temperature with whipped cream or vanilla ice cream, if desired.


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