Traditional recipes

Fresh Pineapple Upside Down Cake

Fresh Pineapple Upside Down Cake

I bought a fresh pineapple along with other fresh fruit for the weekend. After a couple of days I decided to make a Fresh Pineapple Upside Down Cake and this dessert was enjoyed by my lake neighbors.

You can use canned pineapple for this recipe but the fresh pineapple was amazing. There was extra pineapple so I chopped and added some in the mixture and enjoyed some for myself! The cook needs to eat too…

I used a 9×9 metal pan. My initial thought was to prepare this in a cast iron pan but mine is at home in Connecticut and I am baking this at our lake house. I do plan on making this again using my cast iron pan.


  • 7 Pineapple slices plus 1 for chopping
  • 2/3 Cups unsalted butter, room temperature
  • 1/2 Cup packed light brown sugar
  • 1 1/2 Cup All Purpose flour
  • 1 Cup white sugar
  • 2 Teaspoons baking powder
  • 1 Teaspoon vanilla
  • 1/2 Teaspoon sea salt
  • 2/3 Cups light cream
  • 1 large egg
  • 1 Tablespoon unsalted butter, melted
  • 1/3 Cup unsalted butter (room temperature)
  • 1/2 Cup packed light brown sugar


Calories Per Serving645

Folate equivalent (total)99µg25%

Riboflavin (B2)0.2mg13.6%

Fresh Pineapple Upside Down Cake #SpringSweetsWeek

I have almost always used a box mix to make pineapple upside down cake. And I’ve almost always used canned pineapple to make it, too. But this time, I thought I’d use fresh pineapple and see how it goes. And you know what? I went AWESOME!

Can you use fresh pineapple to make pineapple upside cake?

Yes. Yes, you can. And having made pineapple upside down cake using fresh pineapple, I don’t think I’ll go back to canned. The fresh pineapple makes this cake taste even more delicious. If that’s even possible.

No, you don’t get those perfect rings to put the cherries in. Well, you could, if you had one of those pineapple corer things, but I don’t. I find one trick ponies to take up too much space in my drawers. And I have a ton of things already in several of them. Frustrates the hubs to no end.

What is upside-down cake?

Originally called skillet cakes, it’s a cake that is baked in a pan where the toppings are on the bottom. Once the cake is baked, you invert it onto a plate putting the cake on the bottom and the toppings on the top. Makes sense, right?

Dating back to the middle ages, skillet cakes were made with seasonal fruits like apples, cherries, and peaches. However, it wasn’t until the 1800’s where the upside-down cake first started appearing in publications. Fast forward a hundred years or so and Dole invented canned pineapple. The rings were pretty in the skillet/upside-down cake technique.

Pineapple upside down cake became really popular after the Hawaiian Pineapple Company (aka Dole) sponsored a contest for pineapple recipes. There were so many pineapple upside down cake recipes submitted the company ran an ad about it. This ad made popularity for this cake soar!

Is pineapple upside down cake easy?

Yes! It’s super easy. I used two bowls because I like mixing the liquid and dry separately before adding the two together. You start the butter and brown sugar, then measure out the dry ingredients. Stir the butter mixture often while you combine all the wet ingredients. By the time everything is combined, the butter mixture should be finished.

Then it’s a matter of slicing the pineapple and plopping in some cherries, if you want. Then you pour the caramel over the pineapple. And then the batter over the caramel. Pop it into the oven. Simple as that. The longest is waiting for it to cook.

Just look at that pineapple upside down cake with fresh pineapple!! Doesn’t it just look fresh and delicious?? Those slices of fresh pineapple with their sweet tart flavor. So good on top of the sweet and simple cake. Just a dollop of ice cream or whipped cream and you’re set for dessert.

The cake is moist and slightly sweet. You don’t want the cake overly sweet because the caramel topping will be sweet enough. It’s a hearty cake and not like a bakery style cake. Not that it’s heavy, but it’s not super light and fluffy. I like that because it goes well with the pineapple.

The cherries floated when I poured the batter over them. I was fine with that. The cherries add for a fun and festive pop of color in the golden cake. And you almost have to have them in a pineapple upside down cake. Right?

Yes, you can make this pineapple upside down cake in a cast iron skillet. If you do that, be careful when placing the pineapple pieces and cherries in the hot skillet. It would add a nice crispy edge around the outside I’d imagine. Sort of like cornbread, I’m thinking.

I made mine in a square pan. I used an 8࡮ nonstick baking pan which worked perfectly. The plate is just a little small on the corners. This caused a little loss of the precious caramel topping to leak out. Make sure your serving plate is large enough for your pan or else this will happen to you, too.

That color is just drool worthy right?

It’s perfectly caramel colored. And it seeps into the cake making a perfect marriage of flavors. I made this pineapple upside down using plain flour. I never have self-rising flour in the house because you can easily make it if you need it. Which you don’t for this recipe. So, not to worry!

You can cut your pineapple for this fresh pineapple upside down cake any thickness you want. I want with a rather thin slice. I didn’t want the pineapple to be super heavy on top. You will need to think about that when you slice the pineapple.

And yes, you can make this pineapple upside down cake without cherries. Or you could use fresh cherries instead of maraschino cherries. You could also make pineapple upside down cake without brown sugar. You simply use pre-made caramel sauce from the ice cream toppings aisle. I have done that in the past and it turns out well.

Ultimate Fresh Pineapple Upside Down Cake

Here&rsquos another Classic! Ultimate Fresh Pineapple Upside Down Cake!

So much caramelized yumminess, it's insane.

Developed centuries ago, this cake has stood the test of time. They used to be cooked in cast iron skillets over an open fire.

Fruit and sugar was added to the bottom of the skillet and cake batter was poured over the mixture. Once cooked, flipping it over onto a plate not only released the cake from the skillet, but showed how pretty the caramelized fruit was on top.

The cake is a fluffy white vanilla cake and it's made with fresh pineapple, brown sugar and butter for the carmelization.

But of course, if you don't have fresh pineapple, you can absolutely use canned pineapple. I had a pineapple I bought at the grocery (ALDI) and have wanted to make this vintage recipe to put on the blog.

Finally getting to it. There's like a million desserts I want to make, but how could I ever leave this off the list? I can't. it's the real deal.

This lovely cake deserves to be put on a pedestal.

This cake was made in an 8 inch pan.

One thing you should know.

Don't use a springform pan.

Lesson learned when you make these types of upside down cakes. Once things start heating up, that glorious butter brown sugar glaze is going to drip and spill in your stove and make a huge mess.

Bake it in a regular 8" buttered cake pan to get ultimate results.

I love bringing back classics and these cakes are not as hard to make as you would think.

You basically cook the fruit with the butter and brown sugar until tender and then place it in the bottom of your pan. Make and dollop the cake batter on top and then smooth out. Bake away!

Leave to stand for 5 minutes then turn out onto your platter.

Serve warm or room temp. We love fresh whipped cream with cherries with ours, but you could add a yummy scoop of vanilla ice cream and caramel topping, whipped cream and a cherry to delight in the Absolute Ultimate Fresh Pineapple Upside Down Cake treat.

Recipe Summary

  • 1 ripe medium pineapple
  • 1 cup unbleached all-purpose flour
  • 1 teaspoon baking powder
  • 1 stick plus 3 tablespoons (5 1/2 ounces) unsalted butter, softened
  • 1/2 cup granulated sugar
  • 2 large eggs, at room temperature
  • 2 tablespoons Cognac or other brandy
  • 2/3 cup light brown sugar
  • 9 fresh cherries, pitted (optional)
  • Vanilla ice cream, for serving

Using a sharp knife, peel the pineapple and remove the eyes. Halve the pineapple lengthwise and cut out the center core. Cut each half crosswise into five 2/3-inch-thick semicircles. Cut one of the semicircles into 3 pieces.

Preheat the oven to 375°. In a small bowl, stir together the flour and baking powder. In a medium bowl, beat 1 stick of the butter until pale and creamy. Gradually beat the granulated sugar into the butter until the mixture is fluffy. Beat in the eggs one at a time, beating well after each addition. Stir in the flour mixture in 3 batches just until smooth. Stir in the Cognac and set aside.

Melt the remaining 3 tablespoons butter in a 9-inch cast-iron skillet if the handle isn't ovenproof, wrap it in foil. Stir in the brown sugar and cook over moderate heat until melted and bubbling, about 3 minutes. Remove the pan from the heat. Arrange the 9 pineapple semicircles in a tight concentric ring in the skillet and fit the 3 small pieces in the center. Cook over moderately high heat for 10 minutes. Turn the pineapple slices and lower the heat so that the mixture simmer vigorously. Cook until the fruit is tender when pierced, about 10 minutes longer. Insert a cherry in the hollow of each semicircle.

Remove the skillet from the heat and spread the cake batter evenly over the hot pineapple it may not completely cover the fruit, but it will spread as it cooks. Bake in the middle of the oven for about 20 minutes, or until the cake springs back when pressed. Let it cool for 10 minutes, then invert the cake onto a large platter. Serve the cake warm with vanilla ice cream.

Upside-down Pineapple Cake

You know me, I love a simple bake, especially one that looks deceivingly like a showstopper with very minimal effort. This upside-down Pineapple Cake is just that! A delicious sponge, topped (bottomed?) with glowing rings of pineapple and gems of glace cherries.

When I first started researching Upside-down Pineapple Cake I was quite surprised by two things…

One: The amount of recipes I found that don’t use glace cherries! I know not everyone is a fan of a glace cherry but to me they are an important part of a pineapple cake, adding a bit of colour and interest, not to mention that sweet, candy-like punch too.

And two: Just how many upside-down cake recipes there is that don’t actually involve any kind of upside-down at all! Instead opting to place the pineapple on top of the sponge. Madness!

Rest assured, this Upside-down Pineapple Cake does indeed use cherries and is a literally upside-down cake, with the fruit baked under the cake, before being flipped onto the plate to reveal it’s true beauty. The eagled-eyed amongst us might even notice that the sponge follows the same recipe as one of our Victoria Sponge cakes .

It’s easy to prepare (depending on how much of perfectionist you are with your pineapples, that is), using just store cupboard ingredients and from a batter to the plate in less than an hour… This cake is the perfect pudding for when you are in need of a bit of sweetness.

And hey, it has fruit! That means it is healthy, right?!


Soft Brown Sugar
Before we add the fruit to the bottom (top?) of our upside-down cake, we add a bit of “cake glue”. In other words, a smearing of sugar and butter/margarine. This not only helps keep the pineapple in place but it adds a nice sweet, almost caramelised-like finish too.

Butter or Margarine
As well as using butter or margarine in our “cake glue”, it goes into the sponge portion of the recipe too. I find margarine to be better and more predictable for sponge cakes but it’s personal preference which you opt for.

This recipe uses tinned pineapple, mostly due to tradition and ease. You could of course try using fresh pineapple, however I worry it could dry out a bit in the baking process.

Glace Cherries
The little gems that compliment the pineapple so well! Be sure to half them so they are a similar thickness to the pineapple slices.

Caster Sugar
The go-to sugar in a sponge cake. Finer than granulated sugar, so mixes in like a dream.

The size of the eggs doesn’t matter too much (I always use medium) but just be sure you’re using free-range eggs.
As with all ingredients when baking a sponge cake, ensure they are at room temperature before starting.

Self-raising Flour
Again, flour is a must in a cake batter and self-raising is used here to allow it to rise. No additional raising agents are required but be sure to sift the flour.

Pineapple Upside Down Cake Origin

One of the earliest mentions of upside down pineapple cake is in a 1925 Gold Medal Flour ad, which featured a golden-brown cake with pineapple slices, cherries and a brown sugar glaze. Pineapple upside down cake is often rooted with the story of Dole Pineapple producing a contest for pineapple recipes after their invention of a pineapple ring cutting rig around 1920.

But Pineapple upside down cakes have a history born before home ovens, when these “skillet cakes” were baked over a fire. The cake was a modern marvel, since it relied on the recently introduced innovations of canned pineapple rings and preserved maraschino cherries.

Considered a classic American cake, pineapple-upside down cake first appeared when canned pineapple become available. But the method of creating a lusciously caramel-like topping for a cake, pastries (like caramel rolls), or bread has a long baking history.

Pineapple upside-down cake’s popularity peaked in the 1950s, but it’s stuck around, becoming just as much of a classic because it’s so easy to make. While it’s been around for a long time, a good cake never goes out of style, so it’s no surprise that classic Pineapple Upside Down Cake recipe is still going strong after decades of popularity.

Fresh Pineapple Upside Down Cake Recipe

PREP 25minsCOOK 40minsTOTAL 1hr 5mins
This is a lovely light cake that’s simple to make. The batter is scented with citrus peel we like to use lime or lemon. Then the batter is smeared over a layer of softened butter, brown sugar, warm cinnamon, and fresh pineapple slices. The final cake is light, with a gooey brown sugar sauce on top. We love using fresh pineapple here, it’s much lighter in flavor than canned. If you’re in a pinch, canned pineapple will work — just be sure to use canned pineapple in the lightest syrup you can find.

Makes 1 (9-inch) cake, 8 slices


12 tablespoons (170 grams) unsalted butter, softened (1 1/2 sticks)

1/2 cup (100 grams) lightly packed brown sugar

2 teaspoons lime or lemon zest

1/2 teaspoon ground cinnamon

8 ounces (225 grams) fresh pineapple, cut into 1/2-inch-thick wedges (about 1/4 pineapple)

1 cup (200 grams) granulated sugar

1 teaspoon vanilla extract

2 teaspoons baking powder

1 1/2 cups (195 grams) all-purpose flour

1/2 cup (125 grams) sour cream or plain yogurt

Position an oven rack in the lower third of the oven and heat oven to 350 degrees F.

Using the back of a spoon, spread 4 tablespoons of the butter over the bottom of a 9-inch cake pan. Scatter the brown sugar and cinnamon evenly over butter. Arrange the pineapple wedges in one even layer over the butter and sugar.

In a large bowl, beat the remaining 8 tablespoons of butter, granulated sugar and zest with an electric mixer on high speed until light and fluffy, 2 to 3 minutes.

Add the egg yolks and vanilla and beat until smooth. Scrape the sides and bottom of the bowl then mix in the baking powder and salt.

Mix in a third of the flour until only a few streaks of flour remain then mix in the remaining flour. Add the egg whites and sour cream and mix just until smooth.

How To Make Pineapple Upside-Down Cake

Step 1: Prepare the pineapple layer

Melt butter in a 9×13 inch non-stick baking pan, then sprinkle with brown sugar and add a layer of pineapple chunks.

Step 2: Make the batter

Mix the dry ingredients (flour, baking powder, sugar and salt) in a large bowl. Add the liquid ingredients (vegetable oil, milk, eggs and vanilla) and mix until smooth. You can mix it with a spoon &ndash no mixer needed!

Step 3: Pour batter over pineapple layer

Pour the cake batter into the baking pan so it evenly covers the pineapple layer.

Step 4: Bake the cake

Bake the pineapple upside-down cake for 1 hour at 350F.

Step 5: Invert the cake

Once the pineapple cake is baked, loosen the sides of the cake from the pan by running the knife around the pan, then put a large platter or baking sheet on top and flip the cake over.

Now the pineapple layer is on top and the pineapple cake is a propper UPSIDE-DOWN pineapple cake :)

Slice the pineapple upside-down cake into squares and enjoy! It is delicious warm or at room temperature!

If you have any pineapple chunks left over after making this cake, use them up to make pineapple salsa, bacon-wrapped pineapple, pineapple pizza or pineapple shrimp stir-fry. Here&rsquos to non-stop pineapple yum!

If you like this easy pineapple upside-down cake, you will love these other easy cake recipes:

Cherry Crumble Cake &ndash so tender and delicious with a sweet cherry filling!

Chocolate Truffle Cake &ndash this is the king of all cakes, chocolate cake with chocolate cream and chocolate truffles on top!

Cinnamon Roll Cake &ndash cinnamon roll in a cake form, this is the easiest way to get your fix of homemade cinnamon rolls!

Chocolate Chip Cookie Cake &ndash it&rsquos like a giant chocolate chip cookie in a cake form, amazing!

  • Topping:
  • 1/2 stick (1/4 cup) unsalted butter (melted)
  • 2/3 cup light brown sugar ( firmly packed)
  • 3 cups fresh pineapple, cut into 1-inch chunks (about 1 pineapple)
  • Cake:
  • 1 1/2 cups all-purpose flour
  • 1 1/2 teaspoons baking powder (double-acting)
  • 1/2 teaspoon salt
  • 1/2 teaspoon cinnamon
  • 1 stick (1/2 cup) unsalted butter (softened)
  • 2/3 cup sugar (granulated)
  • 2 large eggs
  • 1 teaspoon pure vanilla extract
  • 3/4 cup milk
  • Garnish: whipped cream or vanilla ice cream

Make the Topping

In a small bowl, stir together the butter and the brown sugar until it's well-mixed and spread the mixture evenly in a well-buttered 9- by 2-inch round cake pan.

Pat the pineapple dry between several thicknesses of paper towels and arrange it evenly on the sugar mixture.

Make the Cake

Preheat the oven to 350 F.

Sift together into a bowl the flour, baking powder, salt and cinnamon.

Place the butter and sugar in another bowl and cream with an electric mixer until the mixture is light and fluffy.

Add the eggs, one at a time, beating well after each addition, and beat in the vanilla.

Add the flour mixture alternately in batches with the milk, beginning and ending with the flour mixture and beating well after each addition.

Pour the batter into the pan, spreading it evenly, and bake the cake in the middle of the oven for 45 to 55 minutes, or until a tester comes out clean.

Let the cake cool in the pan on a rack for 15 minutes, then run a thin knife around the edge and invert the cake onto a plate.

Serve the cake warm or at room temperature with the whipped cream or vanilla ice cream.

Emphasize the tropical flavor of pineapple upside-down cake by adding maraschino cherries to the topping. Arrange them along with the pineapple on top of the topping sugar mixture, alternating each one.

Substitute rings for chunks for a pretty presentation. Cut fresh pineapple into rings or use canned pineapple rings.

Use a Bundt cake pan for a more spectacular presentation. Use fresh or canned pineapple rings with this pan. Cut the rings in half and stand them vertically against the sides of the pan for an interesting look.

Pineapple Upside-Down Cake

Preheat the oven to 400 degrees . Spray a parchment lined 9-inch round cake pan with unflavored cooking spray. Melt 1 stick of the butter and set aside.

In a small saucepan, melt the remaining 4 tablespoons of butter with the brown sugar over medium heat, about 3 minutes. Spread the butter-and-sugar mixture in the bottom of the prepared cake pan. Distribute the pineapple slices evenly over the mixture and set the pan aside.

In a large bowl, combine the flour, baking powder, sugar and salt. In a medium bowl, beat together the egg, milk and the reserved melted butter. Stir the liquid ingredients into the dry ingredients until well combined the batter will be thick. Using a rubber spatula, scoop the batter into the cake pan, spreading it until it reaches the sides of the pan.

Bake the cake until the top is golden brown and a toothpick inserted in the center comes out clean, about 30 to 35 minutes.

Let the cake cool for 15 minutes. Place a serving plate over the cake pan and invert. Slowly lift off the pan and serve.