Pineapple Upside Down Cake

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The single most requested cake at our family and friend gatherings is my father’s pineapple upside down cake. He’ll look for almost any excuse to make it, and we never get tired of it.

The cake is dense, like a sour cream pound cake, with ground almonds in the flour to give it even more substance and a slight almond flavor. The caramel pineapple topping is so good, you’ll want to pick every crumb.

Pineapple Upside Down Cake

There are a couple of ways to do the topping. The easiest way is by melting brown sugar and butter. My father will also often make a caramel base from caramelizing white sugar (instructions at the end of the recipe for this alternative).

Pineapple Upside Down Cake Recipe

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  • Prep time: 15 minutes
  • Cook time: 1 hour, 20 minutes

If you don't have a high-sided 10-inch cake pan, you might try making this in a springform pan. Line the inside with foil so the caramel doesn't leak, and bake on a rimmed baking sheet just in case it does. (Thanks to a tip in the comments!)

Ingredients

Topping:*

  • 1 cup of firmly packed dark brown sugar
  • 1/2 cup unsalted butter
  • 1 can (20 oz) of pineapple slices

Cake:

  • 1 1/2 cups all purpose flour
  • 6 Tbsp cake flour
  • 6 Tbsp of ground almonds (from about 2 oz of whole almonds)
  • 3/4 teaspoon baking powder
  • 1/2 teaspoon salt
  • 1 3/4 cups of sugar
  • 1 cup (2 sticks) unsalted butter at room temperature
  • 4 eggs
  • 3/4 teaspoon vanilla extract
  • 3/4 cup sour cream

Method

1 Start by making the caramel topping. Take brown sugar and butter and combine and melt in a saucepan on medium heat until sugar dissolves and the mixture is bubbly, this should take several minutes. (After sugar melts, don't stir.) Pour mixture into a 10 inch diameter stick-free cake pan with 2 inch high sides. Arrange pineapple slices in a single layer ontop of the caramel mixture.

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2 Preheat oven to 325° F. Whisk the flours, ground almonds, baking powder, and salt in a large mixing bowl. In a separate bowl, use an electric mixer to beat the sugar and butter together until light. Add eggs one at a time, beating after each addition. Beat in the vanilla. Add dry ingredients alternately with sour cream in 2 additions each, beating well after each addition. Pour cake batter over caramel and pineapple in pan.

3 Bake cake until tester inserted into the center comes out clean, about 1 hour to 1 hour 15 minutes. Cool cake in pan on a rack for 10 minutes. Turn cake out onto a platter. Serve warm or at room temperature.

Makes 12 to 14 servings.

* Note an alternative topping: 2 cups granulated sugar, 1/2 cup water, 1/4 cup butter. Combine sugar and water in a medium saucepan. Heat on medium until all sugar is dissolved. Increase heat to medium high and bring to a boil. Boil until syrup becomes warm amber in color (about 10 minutes). Add 1/4 cup butter, carefully as it will foam up a bit. Swirl the pan so that the butter is all incorporated, stirring with a wooden spoon if necessary. Remove from heat and pour out into cake pan. Continue with recipe as noted.

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Links:

History of Pineapple Upside Down Cake from Tori Avey

Pineapple Upside Down Cake

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Showing 4 of 211 Comments

  • Candice Atkinson

    It was really enjoyable, students tried it for the first time and it was super for them. The right pan is needed to prevent dripping of the syrup.

  • Hayley

    Thank you for this excellent recipe. I made two cakes. One cake was your recipe and the other a gluten free version. The same recipe except with Gluten free flour and 1/4 teaspoon of Baking Soda and 1 1/4 teaspoon of Baking powder. I left out the cake flour mix. I made them both in a 12 inch Skillet and baked them in the skillet. They were amazing! This recipe got voted number one on the desserts list! Which I was very proud of.
    I also added coconut to the caramel mixture before laying down the pineapples which added extra toffee crunch.
    The gluten-free version came out really light and fluffy which was excellent and your recipe came out more dense, people loved both for different reasons.
    Such a delicious recipe. Adding it to the fav’s list! thank you!!

  • Gerry

    When we made this, we put red glacee cherries in the pineapple holes

  • Nathan

    Do I have to use the 6tbsp of cake flour? I am going to use almond flour which is easier than grinding almonds. Can I use some extra almond powder instead of the cake flour?
    Thanks.
    Nathan

  • Anonymous

    For those who want to follow the recipe and don’t have cake flour on hand. I found the following substitution:

    For 1/2 cup of cake flour: put 1 tbsp of cornstarch in a 1/2 cup measuring cup and fill the rest of the cup with all purpose flour. This will give you a total of 1/2 C of cake flour. Mix well and set aside. Make sure you measure out 6 tbsp for the recipe since this mixture makes a bit more than the recipe calls for. It’s the first time trying this recipe. It’s in the oven now, so we shall see…

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