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A cranberry pineapple upside down cake.

Cranberry Pineapple Upside Down Cake

  • Author: Rebecca Blackwell
  • Prep Time: 60 minutes
  • Cook Time: 35 minutes
  • Total Time: 1 hour 35 minutes
  • Yield: Six 4-inch cakes


Tender little individual sized Cranberry Pineapple Upside Down Cakes are baked with pineapple slices, tart cranberry sauce, and a buttery brown sugar caramel glaze.


For the Cranberry Sauce: (*If you’d rather use prepared cranberry sauce, you’ll need 1 cup)

  • 6 oz fresh or frozen cranberries
  • 1/21 cup granulated sugar
  • 1 tbsp orange zest
  • 1 tbsp freshly squeezed lemon juice
  • Salt and pepper

For the Caramel Glaze and Pineapple:

  • 1/2 cup (4oz.) butter, at room temperature
  • 1 cup dark brown sugar
  • 2 tbsp corn syrup
  • 2 tsp pure vanilla extract
  • 1/2 tsp salt
  • 6 sliced rings of canned pineapple

For the cakes:

  • 4 large eggs, at room temperature
  • 3/4 cup granulated sugar, divided
  • 1/2 cup (4 oz) butter
  • 1/4 cup dark brown sugar
  • 3 tsp pure vanilla extract
  • 1 1/2 cups unbleached all-purpose flour
  • 1/4 cup cornstarch
  • 1 tsp baking powder
  • 1 tsp table salt (1 1/4 tsp kosher salt)
  • 1/2 cup buttermilk, at room temperature


Make the Cranberry Sauce:

  1. Add all but 1/4 cup of the cranberries to a heavy bottomed sauce pan. Add 1/2 cup sugar, orange zest and lemon juice to the pan.
  2. Cook over medium-low high heat, stirring frequently, until the cranberries are soft and all the sugar has dissolved. Increase the heat to medium-high and cook until the cranberries burst – about 5-6 minutes.
  3. Reduce the heat to low and stir in the reserved cranberries. Taste and add up to 1/2 cup more sugar depending on how sweet you like your cranberry sauce. (I like my cranberry sauce tart, so usually don’t add any additional sugar. But, make sure to taste it and adjust it to your personal liking.)
  4. Remove the pan from the heat and sprinkle in a bit of salt and pepper, tasting until you get the amount that tastes right to you.
  5. Allow the cranberry sauce to cool to room temperature and then store in a jar or other airtight container in the refrigerator for up to 2 weeks in the refrigerator.

Prep the cake pans and make the caramel glaze:

  1. Prepare six 4-inch springform pans as follows: Grease the bottoms and sides of the pans with vegetable shorting. Cut out 6 circles of parchment paper that are about 1/2 inch larger than the bottoms of the pans. Press the parchment into the bottoms of the pans – it should come up the sides of the pan about 1/2-inch on all sides. Lightly grease the parchment paper and shake some flour around in the pans to coat. The parchment paper will help keep the caramel sauce from leaking out.
  2. Add all the glaze ingredients except the pineapple slices to the bowl of a standing electric mixer. Beat on high speed for 4-5 minutes, stopping to scrape down the sides of the bowl several times, until the mixture is light and fluffy.
  3. Divide the glaze evenly between all six pans and use your fingers to pat the glaze into a somewhat even layer across the bottom of the pans.
  4. Divide the cranberry sauce evenly between all six pans and using a small spoon, or your fingers, spread the sauce evenly over the top of the caramel glaze. Top with a pineapple ring and press it down gently into the cranberry sauce. (You can also reverse the fruit layers so that the pineapple slice is visible on the tops of the cakes when you unmold them: glaze, pineapple slice, cranberry sauce.)

Make the cake batter:

  1. Preheat the oven to 350 degrees.
  2. Separate the egg whites from the yolks. Using an electric mixer, beat the egg whites until frothy. With the mixer running, gently sprinkle in 1/4 cup of the granulate sugar and beat until the egg whites are glossy and form peaks that hold their shape if you lift the beater from the egg whites. Set aside.
  3. Add the butter, remaining 1/2 cup granulated sugar and brown sugar to the bowl of an electric mixer. Beat on high speed for 4-5 minutes, stopping several times to scrape down the sides of the bowl, until the mixture is light and fluffy. Add the vanilla and beat until incorporated.
  4. Add two of the egg yolks and beat on medium speed until they are completely incorporated. Scrape down the sides of the bowl. Add the remaining two egg yolks, beat until incorporated and scrape down the sides of the bowl.
  5. In a separate bowl, add the flour, cornstarch, baking powder and salt and using a wire whisk, stir to combine.
  6. Add the flour mixture in 3 alternating additions with the buttermilk, scraping down the bowl and beating on low after each addition just long enough to incorporate: Flour, buttermilk, flour, buttermilk, flour.
  7. Using a wooden spoon or rubber spatula, gently fold the beaten egg whites into the batter, stirring just until incorporated.
  8. Divide the batter between the six pans. The batter will come nearly up to the tops of the pans.
  9. Line a baking sheet (preferably a rimmed baking sheet) with aluminum foil. This will save your oven if any of the glaze manages to seep from the pans while baking. Place the cakes on the foil lined baking sheet and bake for about 30-35 minutes – until a toothpick inserted into the center of one of the cakes come out without evidence of batter.
  10. Remove the cakes from the oven and allow them to rest for 5 minutes. With a gloved hand or a towel to protect your hands from the hot pans, flip the cakes over, in their pans, one by one onto individual plates or a large serving platter. Wait about 5 minutes before releasing the sides of the pans to allow the glaze to trickle down into the cakes. Release the sides of the springform pans, and remove the pan bottoms and the parchment paper.
  11. Serve the cakes warm. They can be stored at room temperature for up to 1 day or in the refrigerator for up to 3 days. To re-warm them, reheat in the microwave on 50% power for 20-30 seconds.

Keywords: upside down cake, pineapple upside down cake, cranberry upside down cake, cranberry pineapple upside down cake, mini cakes, Christmas cake, holiday recipe, butter cake