Name: Cranberry Pineapple Upside Down Cake
Prep time: 1 h
Cook time: 35 min
Total time: 1 h 35 min
Yield: 4
Ingredients: 6 oz fresh or frozen cranberries; 1/2 - 1 cup granulated sugar; 1 tbsp orange zest; 1 tbsp freshly squeezed lemon juice; Salt and pepper; 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; 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

Jump to Recipe

Buttery little Cranberry Pineapple Upside Down Cakes baked with pineapple slices, tart cranberry sauce, and gooey brown sugar caramel glaze.

"Delicious cake! The combination of tart cranberries, sweet pineapple, and moist airy cake was incredible! Loved every bite:) Making your own cranberry sauce is definitely worth it - nothing from a can could compare and it’s really not that much effort! I used the juice from my zested orange instead of lemon juice - it was perfect!" -Valerie

Individual Cranberry Pineapple Upside Down Cakes with Brown Sugar Caramel Glaze

OMG. THESE CRANBERRY PINEAPPLE UPSIDE DOWN CAKES ARE SO GOOD.

This recipe makes 6 little individual sized cakes. And yet, you will not see one picture in this post that actually includes 6 cakes because I ate one before I could even take the pictures. Self control flew the coop the second I took these out of the oven.

Besides not having to deal with slicing and serving one large cake, one of the points of baking smaller, individually portioned desserts IS portion control. And these cakes are totally big enough to be split between 2, or even 4 people. Even still. I ate that entire cake in one sitting and am currently eyeing another.

What can I say? There is something about the combination of tender butter cake coated in tart fruit and buttery brown sugar caramel sauce that I can't resist. More accurately - that I don't want to resist. No regrets. That little cake just made my whole morning.

Gooey Butter and Brown Sugar Caramel Glaze

The ooey-gooey topping - which is actually baked on the bottom so that it ends up on top of the cake when you flip the cakes out of the pan after baking - is what makes an upside down cake an upside down cake. Otherwise, it's just a cake covered in some fruit.

The fruit gets baked along with the cake, concentrating its flavor and sweetness, and flavoring the cake itself. PLUS, there is a butter and brown sugar caramel glaze that soaks right down into the cake, dripping down the sides all messily like a good sauce should.

The gooey buttery brown sugar glaze is actually the same mixture I use for caramel rolls. The glaze is made by beating butter and brown sugar together for several minutes. This coats all those little sugar molecules with butter, ensuring that the sugar doesn't crystalize while it bakes, creating a caramel sauce that is smooth and silky.

Sweet pineapple slices and tart cranberry sauce

These little upside down cakes are topped with both a slice of pineapple and a generous amount of cranberry sauce, a delicious sweet-tart combination of flavors and textures. But, when assembling them, you have a decision to make: Do you want the pineapple slice to end up on top of the cakes or under the cranberry sauce?

I wanted them to look all Christmas-y, and liked the idea of little cakes completely coated with red cranberries. So, in mine, as you can see, the pineapple slice isn't visible until you cut into the cakes. It's like a little present you have to unwrap.

But, putting the pineapple on top would also be lovely. Or leave out the pineapple altogether. They're your upside down cakes. Do as you like.

A slice of A cranberry pineapple upside down cake.

I used homemade cranberry sauce, but you could purchase it pre-made if you like

The important thing if you're using purchased, pre-made cranberry sauce is that it's really good quality, with chunks of cranberries. Avoid the kind that comes in a can and is the consistency of jello.

The fruit is the star of these cakes, and if it doesn't taste amazing to start with, it won't taste amazing on top of the cake.

Homemade cranberry sauce is quick and easy to prepare and gives you the advantage of being able to control how sweet or tart it is. I've included my favorite method in the recipe below, which contains an option about how much sugar you include. I like mine on the tart side, so I use the minimum amount of sugar. But, taste as you go, and add as much as you like.

Upside Down Cake is Best Served Warm

Upside down cake is the kind of dessert that's most delicious right after baking, while still warm from the oven. It's the caramel sauce. As with caramel rolls, it's most delicious while still warm and oooey-gooey. If you're serving and eating these hours after removing them from the oven, just pop them in the microwave at 50% power for 20-30 seconds to warm them up a bit.

If you really want to take these over the top, serve them with a scoop of vanilla or caramel ice cream.

Serve the cakes whole or as tiny slices

As with the mini almond cakes with cranberry sauce, I like to bake these in little 4-inch springform pans. The removable sides just make the cakes so much easier to remove from the pans. Little 4-inch cakes make for a good sized single serving. Or, cut them into adorable little slices.

You could also forget the whole mini thing and bake this cake in one 9 or 10-inch pan.

Used in this recipe:

More mini dessert recipes:

If you give this recipe a try, let me know! Leave a comment, rate it, or take a picture and tag it #ofbatteranddough on Instagram.

📖 Recipe

Cranberry Pineapple Upside Down Cake

Yield: Six 4-inch cakes

Prep Time: 1 hour

Cook Time: 35 minutes

Total Time: 1 hour 35 minutes

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

Ingredients

(*If you'd rather use prepared cranberry sauce, you'll need 1 cup)

6 oz fresh or frozen cranberries
½ - 1 cup granulated sugar
1 tablespoon orange zest
1 tablespoon freshly squeezed lemon juice
Salt and pepper

For the Caramel Glaze and Pineapple:

½ cup (4oz.) butter, at room temperature
1 cup dark brown sugar
2 tablespoon corn syrup
2 teaspoon pure vanilla extract
½ teaspoon salt
6 sliced rings of canned pineapple

For the cakes:

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

Instructions

Make the Cranberry Sauce:

Add all but ¼ cup of the cranberries to a heavy bottomed sauce pan. Add ½ cup sugar, orange zest and lemon juice to the pan.
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.
Reduce the heat to low and stir in the reserved cranberries. Taste and add up to ½ 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.)
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.
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:

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 ½ 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 ½-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.
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.
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.
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:

Preheat the oven to 350 degrees.
Separate the egg whites from the yolks. Using an electric mixer, beat the egg whites until frothy. With the mixer running, gently sprinkle in ¼ 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.
Add the butter, remaining ½ 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.
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.
In a separate bowl, add the flour, cornstarch, baking powder and salt and using a wire whisk, stir to combine.
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.
Using a wooden spoon or rubber spatula, gently fold the beaten egg whites into the batter, stirring just until incorporated.
Divide the batter between the six pans. The batter will come nearly up to the tops of the pans.
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.
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.
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.

© Of Batter and Dough. All images & content are copyright protected. Please do not use my images without prior permission. If you want to republish this recipe, please re-write the recipe in your own words, or link back to this post for the recipe. Some of the links above are affiliate links, which pay me a small commission for my referral at no extra cost to you! Thank you for supporting Of Batter and Dough.