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  1. Food and Cooking
  2. Recipes
  3. Pineapple Upside-Down Cake

Pineapple Upside-Down Cake

It's a retro dessert fit for a crowd!

By Leah PerezPublished: Apr 10, 2023
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the pioneer woman's pineapple upside down cake recipe
Caitlin Bensel
Yields:
12 - 16 serving(s)
Prep Time:
30 mins
Total Time:
1 hr 30 mins
the pioneer woman's pineapple upside down cake recipe

From the iconic pineapple rings to the bright red cherries to the fluffy yellow cake, pineapple upside-down cake is one of the most recognizable retro American desserts. Back in the 1920s, the Dole pineapple company sponsored a contest for pineapple recipes. The winner by far was pineapple upside-down cake, inspiring the company to run an advertisement with the recipe, and increasing the cake’s popularity exponentially! It is competitions such as those put on by big names like Pillsbury and Betty Crocker that gave us peanut butter blossoms and French silk chocolate pie. But chocolate desserts aside, this tropical fruit dessert not only connected American households to one of Hawaii’s top crops, it also contributed to a completely new way of sharing recipes. Rather than using community-run cookbooks or word of mouth, the same recipe could spread from Portland, Oregon, to Knoxville, Tennessee, through paper publications and ingredient labels. And today, through beautiful blogs…

What is an upside-down cake?

True to its name, an upside-down cake is baked so that the eventual top of the cake is baked on the bottom. After the cake is ready, it's inverted onto a serving platter with the glistening caramel-covered fruit or nuts eliminating any need for frosting or other decorating. A nice dollop of whipped cream or ice cream over a piece of warm cake would put this dessert over the top! Usually made in an 8- to 10-inch cake pan or skillet, this recipe uses a 13x9-inch cake pan for a large sheet cake that will feed a crowd.

How do I make sure my upside down cake doesn’t stick?

The number one way to make sure a cake does not stick is to properly prepare the pan. While using a baking pan with nonstick coating does help, sometimes you want a little extra assurance when dealing with sticky caramel and finicky fruit. An easy, no-fuss way to grease a pan is to use baking spray with flour. A nice rubbing of butter and a thin coating of flour also does the trick. In order to keep the fruit in place and protect the caramel from sticking, line the bottom of the pan with parchment. A smooth stovetop caramel is also key to the perfect upside-down cake. This recipe uses reserved pineapple juice and cornstarch to ensure the caramel stays nice and velvety.

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Ingredients

  • Baking spray with flour

  • 1

    15-ounce can pineapple slices in juice

  • 1

    8-ounce can pineapple slices in juice

  • 2 cups

    plus 2 tablespoons granulated sugar, divided

  • 1 Tbsp.

    cornstarch

  • 12

    maraschino cherries 

  • 1 3/4 cups

    unsalted butter, softened and divided

  • 3/4 cup

    packed light brown sugar

  • 1 1/2 tsp.

    kosher salt, divided

  • 1 1/2 tsp.

    vanilla extract

  • 3

    large eggs, room temperature

  • 3 cups

    all-purpose flour

  • 2 tsp.

    baking powder

  • 1 tsp.

    baking soda

  • 1 cup

    sour cream, room temperature

  • Ice cream, to serve

  • Whipped cream, to serve

Directions

    1. Step 1Preheat the oven to 350°F. Spray a 9x13-inch baking pan with baking spray with flour. Line the bottom with parchment paper; do not spray again.
    2. Step 2Drain the pineapple slices and reserve the liquid. Pat the slices dry with paper towels. Place the pineapple in a large bowl and sprinkle with 2 tablespoons of sugar and the cornstarch, tossing to coat. Place the pineapple in the prepared pan. Add the cherries to the pineapple centers. 
    3. Step 3In a medium stainless-steel skillet, melt ¾ cup of the butter over medium heat; stir in the brown sugar and ½ teaspoon of salt. Bring the mixture to a simmer; cook until the sugar is melted and fragrant, about 3 minutes. Slowly pour in 3 tablespoons of the reserved pineapple juice, whisk until combined and smooth. Pour the caramel over the pineapple.
    4. Step 4In the bowl of a stand mixer, beat the remaining 1 cup of butter, the remaining 2 cups of granulated sugar, and vanilla with a mixer at medium speed until creamy, 2 to 3 minutes, stopping occasionally to scrape sides of bowl. Add the eggs, one at a time, beating well after each addition.
    5. Step 5In a medium bowl, whisk together the flour, baking powder, baking soda, and the remaining ½ teaspoon of salt. Gradually add the flour mixture to the butter mixture alternately with the sour cream, beginning and ending with the flour mixture, beating just until combined after each addition. Carefully dollop and spread the batter onto the pineapple in the pan.
    6. Step 6Bake for 50 minutes. Place a piece of foil on top of the cake to prevent excess browning and bake until a wooden pick comes out clean, 15 to 20 minutes more. Remove the foil and let the cake cool in the pan on a wire rack for 10 minutes. Run a knife around the sides of the cake to loosen; carefully invert the cake onto a serving plate, removing the parchment. Let cool for at least 10 minutes before slicing.
    7. Step 7Serve warm, room temperature, or cold with ice cream or whipped cream.

Tip: Serve the cake with coconut ice cream for a dessert-spin on a piña colada.

Tip: Save the extra reserved pineapple juice for mixed drinks!

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