Pineapple Upside Down Cake

Easy pineapple upside-down cake packed with buttery and vanilla flavors and tender crumb and crowned with canned pineapple slices and maraschino cherries.

With upside-down cakes we work in the opposite direction: we lay down the toppings first, and cover it with cake batter, but once the cake is baked, we flip it. And the bottom becomes the top of the cake – easy, stunning, genius!

A sweet and tart memory from childhood, this cake is definitely one of the pineapple recipes I love to make – it tastes great and is a naturally beautiful and colorful centerpiece.

Why You’ll Love This Recipe

• An easy recipe that makes a generous amount of cake. Quick too, without the need to use a boxed cake mix. The big upside of this cake for me is that it doesn’t require any other frosting, glazes, or toppings. Less work for us!
• Classic pineapple upside-down cake recipe as it uses canned pineapple rings and maraschino cherries. And it looks stunning and reminds me of childhood.
• The texture and flavors. The dense cake is moist, soft, buttery, and sweet and the caramelized pineapple rings are just delightful and burst with juices when you bite.
• Delicious cake for a dessert table at your party that can make 6 to 12 slices. A great bonus is that it is not overly sweet.

Ingredients Notes

Pineapple Topping 

• Unsalted butter. Melted butter will be the first layer of the cake in the pan and it will then cook into pineapples and cake batter together with brown sugar. Just saying that I feel my mouth watering! Using too much butter is one of the reasons to get a soggy pineapple upside down cake so be careful to follow the instructions closely.
• Brown sugar. Light brown sugar has fewer molasses and adds a more subtle caramel flavor, while dark brown sugar will make caramelized pineapple rings taste stronger.
• Pineapple slices + save the juice for the cake batter. I use canned pineapple rings. Pat every pineapple slice dry to make sure the cake won’t become soggy. You are welcome to use fresh pineapple too, try to save as much juice as you can, but if it is not enough to fil 1/4 cup, use a bit of store-bought natural pineapple juice in the batter. Not ideal, but possible.
• Maraschino cherries or glacé cherries, pat dry to avoid soggy cake. I don’t recommend using fresh cherries. They don’t look the same once baked and have tart flavor compared to maraschino cherries soaked in syrup and pretty much holding the shape even after being baked.

Pineapple Cake Batter

• All-purpose flour or cake flour + baking powder, baking soda, and salt. The classic cake base.
• Unsalted butter softened at room temperature
• Granulated sugar
• Egg whites make a lighter cake than if you use whole eggs or yolks.
• Sour cream for rich moist cake. You can also use plain yogurt, buttermilk, or vegan cream, but I find sour cream gives the best results.
• Pineapple juice (saved from the can of slices)
• Milk/coconut milk for dairy-free recipe Milk helps us make a tender cake with moist crumbs and rich flavor.
• Vanilla extract

Kitchen Equipment

• 8×10 baking dish (you can use a 9×13 if that’s what you have) or 8 or 9-inch round cake pan. For a more rustic look, this pineapple upside-down cake can be made in a cast iron skillet. a 9-10-inch cast iron pan would work.
• Microwave-safe bowl to melt butter.
• Optional, cake stand or plate for serving.

How To Make The Best Pineapple Upside-Down Cake

First Layer: Melted Butter And Brown Sugar Mixture

1. Preheat the oven to 350 degrees F.
2. Grease an 8×10 baking dish with cooking oil or non-stick spray.
3. Starting with the “topping”, add the melted butter to the bottom of the prepared cake pan.
4. Sprinkle brown sugar evenly in a thin layer on top of the melted butter.

Second Layer: Pineapple Slices And Cherries

1. Arrange pineapple slices on top of the brown sugar in an even layer.
2. Insert a maraschino cherry into the center of each pineapple ring, and in all of the open spaces where the pineapple is not covering the brown sugar. 
3. Set the dish aside to work on the cake batter.

Third Layer: Pineapple Vanilla Cake Batter

1. Cream the butter and sugar together in the bowl of a stand mixer until it is well blended and smooth.
2. Add the wet ingredients: mix in in the egg whites, sour cream, pineapple juice, milk, and vanilla extract.
3. Mix in dry ingredients: Slowly stir in the flour, baking powder, baking soda, and salt. Scrape down the sides and then increase the speed and beat until well blended.
4. Pour cake batter on top of the pineapple in the baking dish.

Bake The Cake & Serve

1.  Bake for 45 minutes or until golden brown and the cake springs back when gently pressed with your finger and the toothpick inserted comes out clean.
2. Let the cake cool for 10-20 minutes before slicing and serving.
3. Run a butter knife along the edge of the cake to release it from the sides of the dish.
4. Flip. Place the serving plate on top of the baking dish, holding the two together firmly. Then invert to flip the cake out of the baking dish and onto the serving plate. 
5. Slice and serve warm with a dollop of vanilla ice cream on the side.

Storage

The pineapple upside-down cake should be stored in the fridge in an airtight container for up to 2 days. 

You can store pineapple upside-down cake in the freezer for 3 months. Let it cool completely and tightly wrap individual slices with plastic wrap and heavy-duty foil to trap all the moisture.

I would not make pineapple upside-down cake ahead of time as it tastes best when fresh and warm.

Substitutions & Variations

• You can easily make the cake vegan or gluten-free by swapping flour and dairy products with GF and plant-based alternatives.
• Cut some rings in halves and add them on the sides of the pan to have fruit to bite into even on the edges of the cake.
• You can use a cake mix instead of making the cake batter from scratch. Homemade cake batter is much denser than the boxed mix. White or yellow cake mix would work.
• Classic pineapple upside-down cake is served with whipped cream (homemade or store-bought) or ice cream.
• I fill the gaps with cherries but if you’d prefer pineapple flavor, use crushed pineapple instead to spread.
• Add spices! Cinnamon and citrus zest would be magical.
• Other fruit. Upside-down cake recipes can be made with the fruits like apples and berries!

Expert Tips For Making Easy Pineapple Upside-Down Cake

• You can serve the cake warm or cold. To serve is warm reheat in the microwave for a few seconds.
• You can refrigerate the layered topping while preparing the cake batter. It helps to make sure all the pineapple slices and cherries are locked in place.
• Put a baking sheet on the rack underneath the cake. The juices from the bottom layer (pineapples and cherries) will bubble up from the sides and sometimes may drip too.

Popular Questions & Troubleshooting

Why Is My Pineapple Upside Down Cake Soggy?

Pineapple slices had too much juice on them and you used too much liquid in the batter. Make sure to dry the pineapple slices and not to use more liquids than instructed.

Under-baked cake will also be quite soggy so make sure to bake until the toothpick inserted in the center comes out clean.

Do You Flip A Pineapple Upside Down Cake When It’s Hot Or Cold?

Once the pineapple upside down cake is done baking and is cooled on the rack slightly (for 20 minutes). Do not let the cake cool completely before you flip it.

You can safely flip the cake while it is still warm, but not when it is hot, as it is too moist and will definitely stick to the bottom of the pan. Meanwhile, when it is cooling, it is setting together with a cake so we would be able to remove it from the cake pan in one go.

What Is The Trick To Flipping Pineapple Upside Down Cake?

The trick to easily flip and remove the pineapple upside down cake from the pan is to wait 15-20 minutes until it is cooler, then run a knife along the sides, top the pan with a serving plate 2″ bigger than the pan, and holding from both sides with oven mitts flip them.

Lightly tap on the pan to make sure the cake isn’t sticking and gently remove the pan.

Is It Better To Make Pineapple Upside Down Cake The Day Before?

No, the pineapple upside-down cake tastes best the same day when the warm cake is still moist and tender. It can last in the fridge for 2 days.

Should You Use Parchment Paper When Baking Pineapple Upside Down Cake?

I don’t use parchment paper to line the baking pan for the pineapple upside-down cake, but I grease all the sides and the bottom with a non-stick cooking spray.

You can use both, cooking spray and parchment paper to be sure the pineapples won’t stick to the bottom.

What Kind Of Pan Is Best For Upside-Down Cake?

To make a pineapple upside-down cake you can use a round cake pan, a rectangular baking dish, a bundt pan, or a cast iron skillet. The fastest baking time is in a cast iron skillet. Pans without coating work better as they reflect the heat and let the cake cook evenly.

If you love this easy cake recipe, you’re going to love these other simple single-layer cakes too. Please click each link below to find the easy, printable recipe!

More Great Pineapple Recipes

Carrot Cake w/ Pineapple

Piña Colada Cupcakes

Punch Bowl Cake

Dirty Pineapple Whip Pops Recipe

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