Pineapple Upside-down Cake

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This pineapple upside-down cake recipe is flavorful and moist. The cake is baked in a single layer and topped with pineapple rings and maraschino cherries.

pineapple upside-down cake with slices taken out — This classic recipe is always a hit and it takes no time at all to make!

Pineapple upside down cakes are baked in a single pan with the toppings in the bottom of the pan. After the cake is baked, it is inverted so the toppings are on top of the cake. This is why it’s called an “upside-down” cake.

Most of us are familiar with this cake from the one in a box by Betty Crocker or Duncan Hines. I grew up eating these and often wanted this cake for my birthday. I prefer fruity desserts over anything else.

I especially love pineapple desserts. I’ve made cupcakes, curd, and frosting with this succulent fruit.

Upside down cakes have been around since before there were ovens. They used to be made in cast iron skillets that were baked over a fire.

The cake is supremely moist with loads of pineapple flavor. And the topping is caramel-y sweet with tender pineapple rings and juicy cherries.

My version is made completely from scratch but it’s so simple and doesn’t take too much time. I adapted it from my spiced apple upside-down cake. That’s a great cake for you to try next.

Why this recipe works:

Butter gives the cake a rich, buttery profile while pineapple juice infuses the batter with a deep pineapple flavor.
Cake flour yields a more compact crumb making it appear dense but it’s actually very light, soft, and tender.
The right amount of butter and brown sugar is used in the topping so it’s not too soggy or lacking in syrup. The balance is just right.

slice of homemade pineapple upside down cake with a fork taking out a bite

Ingredients

Here’s what you need to make this classic pineapple upside-down cake.

Butter: Unsalted sweet cream butter is what I use for the topping and cake batter. Regular unsalted butter works just fine also.
Sugar: The topping is made with light brown sugar and the cake is made with granulated sugar.
Flour: Cake flour is going to give you the best results. It yields an incredibly soft cake texture.
Leavening: You need baking powder and baking soda to give the cake rise.
Salt: A little salt is needed to balance the sweetness.
Pineapple: A 20-ounce can of pineapple rings works beautifully with this recipe.
Cherries: Use maraschino cherries found in a jar.
Vanilla extract: Just a splash of quality vanilla makes all the difference.
Eggs: Two eggs are required for this cake and make sure they are at room temperature.

Can I use fresh pineapple and cherries instead of canned?

Fresh pineapple and cherries produce more juice during cooking and will prevent the topping from becoming sticky-sweet. In other words, the topping will be thin and runny.

How to make pineapple upside-down cake

Make the topping. Heat the butter and sugar in a saucepan over medium-low heat until fully melted and creamy. The mixture will bubble slightly.

Pour the melted butter and brown sugar mixture into the bottom a greased 9-inch round cake pan. Spread it so it evenly coats the bottom. Arrange pineapple slices over the top and place a cherry in the center of each pineapple.

You can arrange the pineapple and cherries any way you wish.

process shots for making pineapple topping

Make the cake batter. In a medium mixing bowl, cream the butter and sugar until light and fluffy. Beat in the eggs and vanilla followed by the pineapple juice.

The mixture may look curdled at this point. This is normal and will come together when you add the flour.

Sift the flour, baking powder, baking soda, and salt into the butter mixture. Mix on low speed until well combined. the batter will be thick.

Spread the batter evenly over the topping in the pan and bake for 35-40 minutes, until a toothpick inserted into the center comes out clean.

Invert the cake. Let the cake cool for 10 minutes in the pan then invert the cake onto a serving platter. Serve the cake warm or at room temperature.

overhead of whole pineapple cake topped with pineapple rings and cherries

When to flip an upside-down cake?

It can be tricky to know exactly when to invert an upside-down cake. You need to let the cake cool enough to not fall apart but if you let it cool too long the topping will stick inside the pan.

I’ve found that somewhere between 5 and 10 minutes is best. Definitely don’t let the cake sit for longer than 10 minutes before you flip it.

How to flip an upside-down cake?

Once the cake has cooled for 5-10 minutes, run a small knife around the edges to loosen it from the sides of the pan.

Choose a cake stand or low plate for a serving platter and place it over the cake pan. Hold the two together and flip. The cake will slowly fall away from the pan on to the platter. I usually let it sit for a minute or two before slowly and carefully lifting the pan off the cake.

Don’t force the cake out of the pan by banging or thrusting it. This can cause the cake to fall apart.

Once the cake is out of the pan you can reposition any pineapples that may shift or stuck to the bottom of the pan.

three slices of classic pineapple upside-down cake on white plates

Storage tips

Like most cakes, pineapple upside-down cakes can be made in advance. Warm the cake slightly after it’s been refrigerated or frozen and it will taste like it was made the same day!

You can warm individual slices in the microwave for 15-30 seconds.

How to store

Keep the cake tightly covered and store it in the refrigerator for up to 3 days. Serve it cold, room temperature, or lightly warmed.

How to freeze

The cake can be tightly wrapped and frozen for up to 3 months. Allow the cake to cool completely then cover it with a couple of layers of plastic wrap followed by a couple of layers of aluminum foil.

Thaw the cake overnight in the refrigerator and serve cold, room temperature, or lightly warmed.

More pineapple recipes to try