Cranberry Pineapple Upside Down Cake: A Perfect Balance of Sweet and Tart

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There’s something undeniably magical about upside-down cakes. They have a way of turning even the simplest ingredients into a show-stopping dessert. The delight of seeing caramelized fruit slowly reveal itself after flipping the cake is a moment worth savoring. But when you add two beloved, contrasting fruits—tart cranberries and sweet pineapple—this Cranberry Pineapple Upside Down Cake becomes something extraordinary. These mini individual cakes offer a harmonious blend of vibrant flavors and textures, making them an ideal treat for any occasion. From their rich, buttery caramel glaze to their tender crumb, this dessert has everything to make it a crowd-pleaser.

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Cranberry Pineapple Upside Down Cake: A Perfect Balance of Sweet and Tart

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There’s something undeniably magical about upside-down cakes. They have a way of turning even the simplest ingredients into a show-stopping dessert. The delight of seeing caramelized fruit slowly reveal itself after flipping the cake is a moment worth savoring. But when you add two beloved, contrasting fruits—tart cranberries and sweet pineapple—this Cranberry Pineapple Upside Down Cake becomes something extraordinary. These mini individual cakes offer a harmonious blend of vibrant flavors and textures, making them an ideal treat for any occasion. From their rich, buttery caramel glaze to their tender crumb, this dessert has everything to make it a crowd-pleaser.

  • Author: Susan
  • Prep Time: 20 minutes
  • Cook Time: 35 minutes
  • Total Time: 55 minutes
  • Yield: 6 individual cakes 1x
  • Category: Dessert, Cake, Brunch
  • Method: Baking
  • Cuisine: American, Tropical
  • Diet: Vegetarian

Ingredients

Scale

Cranberry Sauce:

  • 6 oz fresh or frozen cranberries
  • ½ to 1 cup granulated sugar (adjust based on how sweet you like it)
  • 1 tablespoon orange zest
  • 1 tablespoon freshly squeezed lemon juice
  • Salt and pepper to taste

Caramel Glaze and Pineapple:

  • ½ cup (4 oz) butter, at room temperature
  • 1 cup dark brown sugar
  • 2 tablespoons corn syrup
  • 2 teaspoons pure vanilla extract
  • ½ teaspoon salt
  • 6 slices of canned pineapple (or fresh pineapple if preferred)

Cake Batter:

  • 4 large eggs, at room temperature
  • ¾ cup granulated sugar, divided
  • ½ cup (4 oz) butter
  • ¼ cup dark brown sugar
  • 3 teaspoons pure vanilla extract
  • 1 ½ cups unbleached all-purpose flour
  • ¼ cup cornstarch
  • 1 teaspoon baking powder
  • 1 teaspoon table salt (or 1 ¼ teaspoons kosher salt)
  • ½ cup buttermilk, at room temperature

Instructions

1. Making the Cranberry Sauce

The key to this recipe lies in making a flavorful cranberry sauce that perfectly balances tartness and sweetness. Start by adding all but ¼ cup of cranberries to a heavy-bottomed saucepan. Add ½ cup of granulated sugar, orange zest, and lemon juice to the pan. As the mixture heats up, you’ll begin to smell the bright citrusy aroma, which will infuse the cranberries and create an irresistible fragrance.

Cook the cranberry mixture over medium-low heat, stirring frequently. The cranberries will soften as the sugar dissolves, and the fruit will begin to release its juices. After about 5-6 minutes, increase the heat to medium-high and cook until the cranberries burst open. This burst marks the perfect moment to stir in the remaining ¼ cup of cranberries, which will retain a bit of texture and prevent the sauce from becoming overly smooth.

Taste the cranberry sauce as it cooks, and add more sugar if you prefer a sweeter result. This is your chance to fine-tune the flavor. If you enjoy a tangy cranberry sauce, feel free to skip the additional sugar—personal preference is key in achieving the right balance. Once you’re satisfied with the flavor, remove the pan from the heat and add a pinch of salt and pepper to enhance the overall taste. Allow the sauce to cool to room temperature before transferring it to a jar. It will keep in the refrigerator for up to two weeks, making it a versatile condiment for other dishes as well.

2. Preparing the Cake Pans and Caramel Glaze

Next, prepare the cake pans for the upside-down assembly. Using six 4-inch springform pans, grease the bottoms and sides with vegetable shortening. To ensure the cakes come out easily, cut six parchment paper circles that are about ½ inch larger than the pan bottoms. Press the parchment paper into the pans, allowing it to slightly rise on the sides. This will help prevent the caramel from leaking during baking.

Grease the parchment paper lightly and dust the pans with flour. This extra layer of protection ensures the cakes will release perfectly after baking, leaving you with beautifully formed individual servings.

To make the caramel glaze, place all of the glaze ingredients—except the pineapple slices—into the bowl of a standing electric mixer. Beat the ingredients on high speed for 4-5 minutes, stopping every now and then to scrape down the sides of the bowl. The mixture will transform into a light, fluffy consistency. This is the key to achieving a caramel glaze that perfectly coats the fruit and adds a luxurious layer of sweetness to the cake. Once the glaze is ready, divide it evenly among the six pans. Use your fingers or a spatula to spread it into a relatively even layer at the bottom of each pan.

Next, spoon the homemade cranberry sauce evenly into each pan, gently spreading it over the glaze. Finally, place a slice of canned pineapple in each pan, pressing it lightly into the cranberry sauce. The layers of caramel, cranberry, and pineapple will create a stunning fruit base for the cakes.

3. Making the Cake Batter

With the pans ready, now it’s time to prepare the cake batter. Preheat the oven to 350°F (175°C).

Start by separating the egg whites from the yolks. In a clean bowl, beat the egg whites until frothy. Gradually add ¼ cup of granulated sugar, continuing to beat until the egg whites form glossy peaks that hold their shape. This step is crucial for achieving a light and airy texture in the cakes, so take your time and ensure the egg whites are beaten well. Once the egg whites are ready, set them aside.

In another mixing bowl, beat the butter, remaining ½ cup of granulated sugar, and brown sugar until light and fluffy. This process typically takes 4-5 minutes of beating on high speed, and it creates a creamy base for the cake. Once the sugar and butter mixture has reached the right consistency, add the vanilla extract and continue beating until well incorporated.

Add the egg yolks one at a time, beating after each addition until fully incorporated. Make sure to scrape down the sides of the bowl to ensure all the ingredients are mixed well. The mixture should be smooth and creamy at this stage.

In a separate bowl, combine the flour, cornstarch, baking powder, and salt. Whisk these dry ingredients together to ensure they are evenly distributed. Gradually add the dry ingredients to the butter mixture, alternating with the buttermilk. Start by adding a third of the flour mixture, followed by half of the buttermilk, then another third of the flour, the remaining buttermilk, and finally the last of the flour mixture. This method ensures the batter remains smooth without overmixing, which is key to achieving the perfect texture.

Once the batter is ready, gently fold the beaten egg whites into the mixture using a rubber spatula or wooden spoon. Take care not to deflate the air in the egg whites; fold them in just until incorporated. This step helps create a light and fluffy cake crumb that will beautifully complement the caramelized fruit.

4. Assembling and Baking the Cakes

Now that the batter is ready and the fruit layers are in place, it’s time to assemble the cakes. Divide the cake batter evenly between the six prepared pans, filling them nearly to the top. Be sure the batter is spread evenly, and avoid overfilling the pans to prevent any spillage during baking. To catch any potential caramel drips, line a rimmed baking sheet with aluminum foil and place the pans on top. This will save your oven from any potential mess.

Bake the cakes in the preheated oven for 30-35 minutes, or until a toothpick inserted into the center comes out clean. You’ll know the cakes are ready when they are golden brown and have a delightful aroma wafting through your kitchen. The pineapples and cranberries will have caramelized, creating an irresistible scent that will leave you eagerly anticipating the final result.

Once the cakes are done, remove them from the oven and allow them to rest for about 5 minutes. This brief resting time ensures that the caramel glaze sets before you flip the cakes over. After 5 minutes, carefully flip each pan over onto a plate or serving platter. Let the cakes sit for another 5 minutes before releasing the sides of the springform pans. This allows the caramel glaze to trickle down into the cake, creating a beautiful, glossy finish.

5. Serving and Storing

Serve the cakes warm for the ultimate dessert experience. The warm caramel glaze, gooey cranberry sauce, and tender cake are a combination that will have your guests coming back for more. These cakes can be stored at room temperature for up to one day or in the refrigerator for up to three days. If you want to reheat the cakes, simply microwave them on 50% power for 20-30 seconds.

Notes

  • Cranberry Sauce: If you’re in a rush or don’t have fresh cranberries, store-bought cranberry sauce will work just as well. You’ll need 1 cup of cranberry sauce to substitute for the homemade version. While the homemade cranberry sauce adds a fresh and vibrant flavor, the store-bought version offers convenience without sacrificing much in terms of taste.
  • Pineapple: Canned pineapple rings are commonly used in upside-down cakes, but you can opt for fresh pineapple as a substitute. Just make sure to slice it thinly to ensure even cooking and a better presentation.
  • Buttermilk Substitute: If you don’t have buttermilk, you can use regular milk combined with a tablespoon of white vinegar or lemon juice. Let the mixture sit for 5-10 minutes before using it in the recipe to mimic the acidity and texture of buttermilk.

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This recipe combines the bold flavors of fresh or frozen cranberries with the bright sweetness of pineapple. The result? A cake that balances the sweetness of caramel with the tartness of cranberry, and the soft, juicy pineapple slices creating a pleasant contrast to the rich and moist cake. Whether you are looking to impress your guests at a holiday dinner or enjoy a special treat for yourself, these mini cakes will leave everyone in awe of their beautiful appearance and irresistible flavor.

The beauty of this recipe is that it makes six perfectly portioned individual cakes, each one a mini masterpiece of caramel, fruit, and fluffy cake. The fact that each cake is its own little serving makes it an ideal choice for a party, a brunch spread, or a cozy family dessert. There’s something undeniably charming about personal-sized cakes, and these Cranberry Pineapple Upside Down Cakes will surely be the star of the show.

Ingredients Breakdown

For this recipe, you will need the following ingredients:

Cranberry Sauce:

  • 6 oz fresh or frozen cranberries
  • ½ to 1 cup granulated sugar (adjust based on how sweet you like it)
  • 1 tablespoon orange zest
  • 1 tablespoon freshly squeezed lemon juice
  • Salt and pepper to taste

Caramel Glaze and Pineapple:

  • ½ cup (4 oz) butter, at room temperature
  • 1 cup dark brown sugar
  • 2 tablespoons corn syrup
  • 2 teaspoons pure vanilla extract
  • ½ teaspoon salt
  • 6 slices of canned pineapple (or fresh pineapple if preferred)

Cake Batter:

  • 4 large eggs, at room temperature
  • ¾ cup granulated sugar, divided
  • ½ cup (4 oz) butter
  • ¼ cup dark brown sugar
  • 3 teaspoons pure vanilla extract
  • 1 ½ cups unbleached all-purpose flour
  • ¼ cup cornstarch
  • 1 teaspoon baking powder
  • 1 teaspoon table salt (or 1 ¼ teaspoons kosher salt)
  • ½ cup buttermilk, at room temperature

Step-by-Step Instructions

1. Making the Cranberry Sauce

The key to this recipe lies in making a flavorful cranberry sauce that perfectly balances tartness and sweetness. Start by adding all but ¼ cup of cranberries to a heavy-bottomed saucepan. Add ½ cup of granulated sugar, orange zest, and lemon juice to the pan. As the mixture heats up, you’ll begin to smell the bright citrusy aroma, which will infuse the cranberries and create an irresistible fragrance.

Cook the cranberry mixture over medium-low heat, stirring frequently. The cranberries will soften as the sugar dissolves, and the fruit will begin to release its juices. After about 5-6 minutes, increase the heat to medium-high and cook until the cranberries burst open. This burst marks the perfect moment to stir in the remaining ¼ cup of cranberries, which will retain a bit of texture and prevent the sauce from becoming overly smooth.

Taste the cranberry sauce as it cooks, and add more sugar if you prefer a sweeter result. This is your chance to fine-tune the flavor. If you enjoy a tangy cranberry sauce, feel free to skip the additional sugar—personal preference is key in achieving the right balance. Once you’re satisfied with the flavor, remove the pan from the heat and add a pinch of salt and pepper to enhance the overall taste. Allow the sauce to cool to room temperature before transferring it to a jar. It will keep in the refrigerator for up to two weeks, making it a versatile condiment for other dishes as well.

2. Preparing the Cake Pans and Caramel Glaze

Next, prepare the cake pans for the upside-down assembly. Using six 4-inch springform pans, grease the bottoms and sides with vegetable shortening. To ensure the cakes come out easily, cut six parchment paper circles that are about ½ inch larger than the pan bottoms. Press the parchment paper into the pans, allowing it to slightly rise on the sides. This will help prevent the caramel from leaking during baking.

Grease the parchment paper lightly and dust the pans with flour. This extra layer of protection ensures the cakes will release perfectly after baking, leaving you with beautifully formed individual servings.

To make the caramel glaze, place all of the glaze ingredients—except the pineapple slices—into the bowl of a standing electric mixer. Beat the ingredients on high speed for 4-5 minutes, stopping every now and then to scrape down the sides of the bowl. The mixture will transform into a light, fluffy consistency. This is the key to achieving a caramel glaze that perfectly coats the fruit and adds a luxurious layer of sweetness to the cake. Once the glaze is ready, divide it evenly among the six pans. Use your fingers or a spatula to spread it into a relatively even layer at the bottom of each pan.

Next, spoon the homemade cranberry sauce evenly into each pan, gently spreading it over the glaze. Finally, place a slice of canned pineapple in each pan, pressing it lightly into the cranberry sauce. The layers of caramel, cranberry, and pineapple will create a stunning fruit base for the cakes.

3. Making the Cake Batter

With the pans ready, now it’s time to prepare the cake batter. Preheat the oven to 350°F (175°C).

Start by separating the egg whites from the yolks. In a clean bowl, beat the egg whites until frothy. Gradually add ¼ cup of granulated sugar, continuing to beat until the egg whites form glossy peaks that hold their shape. This step is crucial for achieving a light and airy texture in the cakes, so take your time and ensure the egg whites are beaten well. Once the egg whites are ready, set them aside.

In another mixing bowl, beat the butter, remaining ½ cup of granulated sugar, and brown sugar until light and fluffy. This process typically takes 4-5 minutes of beating on high speed, and it creates a creamy base for the cake. Once the sugar and butter mixture has reached the right consistency, add the vanilla extract and continue beating until well incorporated.

Add the egg yolks one at a time, beating after each addition until fully incorporated. Make sure to scrape down the sides of the bowl to ensure all the ingredients are mixed well. The mixture should be smooth and creamy at this stage.

In a separate bowl, combine the flour, cornstarch, baking powder, and salt. Whisk these dry ingredients together to ensure they are evenly distributed. Gradually add the dry ingredients to the butter mixture, alternating with the buttermilk. Start by adding a third of the flour mixture, followed by half of the buttermilk, then another third of the flour, the remaining buttermilk, and finally the last of the flour mixture. This method ensures the batter remains smooth without overmixing, which is key to achieving the perfect texture.

Once the batter is ready, gently fold the beaten egg whites into the mixture using a rubber spatula or wooden spoon. Take care not to deflate the air in the egg whites; fold them in just until incorporated. This step helps create a light and fluffy cake crumb that will beautifully complement the caramelized fruit.

4. Assembling and Baking the Cakes

Now that the batter is ready and the fruit layers are in place, it’s time to assemble the cakes. Divide the cake batter evenly between the six prepared pans, filling them nearly to the top. Be sure the batter is spread evenly, and avoid overfilling the pans to prevent any spillage during baking. To catch any potential caramel drips, line a rimmed baking sheet with aluminum foil and place the pans on top. This will save your oven from any potential mess.

Bake the cakes in the preheated oven for 30-35 minutes, or until a toothpick inserted into the center comes out clean. You’ll know the cakes are ready when they are golden brown and have a delightful aroma wafting through your kitchen. The pineapples and cranberries will have caramelized, creating an irresistible scent that will leave you eagerly anticipating the final result.

Once the cakes are done, remove them from the oven and allow them to rest for about 5 minutes. This brief resting time ensures that the caramel glaze sets before you flip the cakes over. After 5 minutes, carefully flip each pan over onto a plate or serving platter. Let the cakes sit for another 5 minutes before releasing the sides of the springform pans. This allows the caramel glaze to trickle down into the cake, creating a beautiful, glossy finish.

5. Serving and Storing

Serve the cakes warm for the ultimate dessert experience. The warm caramel glaze, gooey cranberry sauce, and tender cake are a combination that will have your guests coming back for more. These cakes can be stored at room temperature for up to one day or in the refrigerator for up to three days. If you want to reheat the cakes, simply microwave them on 50% power for 20-30 seconds.

Tips for Substitutions and Variations

  • Cranberry Sauce: If you’re in a rush or don’t have fresh cranberries, store-bought cranberry sauce will work just as well. You’ll need 1 cup of cranberry sauce to substitute for the homemade version. While the homemade cranberry sauce adds a fresh and vibrant flavor, the store-bought version offers convenience without sacrificing much in terms of taste.
  • Pineapple: Canned pineapple rings are commonly used in upside-down cakes, but you can opt for fresh pineapple as a substitute. Just make sure to slice it thinly to ensure even cooking and a better presentation.
  • Buttermilk Substitute: If you don’t have buttermilk, you can use regular milk combined with a tablespoon of white vinegar or lemon juice. Let the mixture sit for 5-10 minutes before using it in the recipe to mimic the acidity and texture of buttermilk.

Conclusion

Cranberry Pineapple Upside Down Cake is more than just a dessert—it’s an experience. With its beautiful layers of caramelized pineapple, tart cranberry sauce, and light, fluffy cake, each bite is an invitation to indulge in a treat that’s both familiar and exciting. Whether you’re baking for a special occasion or simply craving something indulgent, this cake will not disappoint. Enjoy every step of the process, and let the end result be a testament to the joy of homemade baking. Happy baking!

Tags:

buttermilk / buttery cake / caramel glaze / cranberry / cranberry sauce / easy dessert / fluffy texture / fresh pineapple / fruit cake / holiday cake / homemade cake / individual cakes / mini cakes / party dessert / pineapple / simple dessert / sweet / tart / tropical dessert / upside down cake

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