Pineapple Upside-Down Cake: A Feast for the Eyes

January 25, 2025

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Pineapple Upside-Down Cake is a delicious yellow cake made even tastier with brown sugar crust, pineapple slices, and maraschino cherries! The pineapple cake is moist, and the brown sugar topping pairs so well with the pineapple, creating a delectable treat.

This is my first ever pineapple upside-down cake recipe, and it sure is a darn good one. I’ve always seen the pictures and eaten it at other houses for parties but never made it for myself. Don’t wait a second longer to try making this easy cake recipe for yourself!

The history of Pineapple Upside-Down Cake

Did you know this retro cake is over 100 years old? Upside-down cakes have been popular for longer than that, but the pineapple version was introduced when the Dole Pineapple Company held a pineapple recipe contest in 1926. The winner was a woman named Mrs. Robert Davis, who submitted a recipe for a pineapple upside-down cake, although thousands of people sent in a similar recipe.

Dole publicized the recipe in magazines and advertisements, and it became a popular dessert, especially in the 50s and 60s.

Ingredients for Pineapple Upside Down Cake.

What ingredients do I need for this delicious cake?

While there are many versions of this iconic cake, this classic recipe comes from The Fannie Farmer Cookbook Thirteenth Edition, p. 586; author, Marion Cunningham; publisher, Alfred A. Knopf, Inc., a division of Random House, Inc.; ISBN 0-394-56788-9.

Gather the necessary ingredients as listed below:

12 tablespoons of unsalted butter (1 ½ sticks)
1 cup dark brown sugar
¼ cup of pineapple juice
8 whole pineapple rings
8 Maraschino cherries
½ cup milk
1 large egg
1 ½ cups all-purpose flour or cake flour
2 teaspoons of baking powder
½ teaspoon of salt
½ cup of granulated white sugar
Whipped cream (optional)

First set of process photos for Pineapple Upside Down Cake.

Do I need any special equipment for this Pineapple Upside-Down Cake?

You need to bake this cake in either a 9-inch cast iron skillet or a 9-inch round cake pan. You’ll also need a slightly larger serving plate or round platter with a lip for flipping the finished cake, as there will be a sugary liquid syrup coming from the cake.

Slices of pineapple cake topped with a brown sugar crust.

Should I use fresh or canned pineapple?

You could use fresh pineapple if you have the time and don’t mind extra work. Most people use canned pineapple for convenience. But there is just something I love about fresh pineapple!

If you use fresh fruit, I recommend using a pineapple corer to peel, core, and slice it. It is so easy and quick, producing a little more than the ¼ cup of juice I needed, too. It’s awesome!

I spent about $10 on it a few years ago at our supermarket, and it was worth the investment. There aren’t too many times I need it, but when I do, it’s such a time saver, and the cleanup is much less than using a knife. I highly recommend it.

set of process photos for Pineapple Upside Down Cake.

How to make Pineapple Upside-Down Cake

Step 1: Prepare the Cake Batter: Preheat the oven to 400 degrees F. Melt 8 tablespoons of butter in a small bowl. Remove from the heat and stir the milk and egg into the melted butter, beating well.

Mix the flour, baking powder, salt, and granulated sugar in a large bowl with a hand mixer on low speed. (You could also use a stand mixer fitted with the paddle attachment.) Then add the egg mixture to the dry ingredients and beat until smooth.

Step 2: Prepare the Skillet: Melt 4 tablespoons of butter in an ovenproof skillet or 9-inch cake pan. Stir in the brown sugar and continue to stir over low heat until it dissolves. Remove from heat and add pineapple juice.

Arrange the pineapple rings in a single layer in the bottom of the pan and place a cherry in the center of each; set aside.

Step 3: Assemble and Bake the Cake: Pour batter over the pineapple slices in the skillet or pan. Bake for about 35 minutes or until a toothpick inserted comes out clean. Let the baked cake cool for 5-10 minutes in the pan on a wire rack.

Step 4: Flip it and Serve: When the cake is done, run a knife around the sides of the pan or skillet. Center a serving plate over the top of the skillet. Wearing oven mitts, carefully flip the cake, then slowly remove the pan to unmold the cake onto the platter.

Allow the cake to cool completely, then slice and serve with some stabilized whipped cream (if desired).

Does Pineapple Upside-Down Cake need to be refrigerated?

Yes, you should refrigerate this cake. It contains perishable ingredients like eggs and butter that can spoil and cause illnesses. You can leave it out at room temperature for a day or two but will be unsafe to eat after that.

How do I store leftover Pineapple cake?

Cover the cake with plastic wrap or store it in an airtight container, then refrigerate it for up to four days. You can eat it cold or let it warm up to room temperature before serving.

Brown sugar topping on cake with pineapple and cherries.

Why is my Pineapple Upside-Down Cake soggy?

There should be a nice puddle of sugary syrup from the cake, but if your cake is outright soggy, you have too much moisture in the cake. The canned pineapple slices and cherries are usually the culprit. Drain them thoroughly, then blot them with a paper towel before adding them to your cake pan.

What if my cake is stuck to the pan?

Remove the cake from the pan while it’s still warm. If you let it cool too long, the brown sugar syrup will start to harden and stick. Try heating the bottom of the pan in a shallow bowl of hot water, then try again.

Next time, you can line your pan with parchment paper and peel that off the pineapple topping after you flip it!

A slice of yellow cake with pineapple and cherries.

More Pineapple Treats

If you love the flavor of pineapple in your desserts, try one of these recipes:

This Pineapple Rum Cake has quickly become a family favorite. With pineapple, dark rum, instant pudding mix, and a boxed cake mix, it’s super easy to put together and tastes even better the next day.
You might also like Pineapple Soak Cake – a super moist, eggless cake full of pineapple and topped with whipped cream or ice cream. It’s a great treat for summer cookouts or anytime!
This Pineapple Bread will be a great treat in the morning alongside your cup of coffee. The toasted coconut on the top also helps you feel like you’re in the tropics! Pineapple and coconut together are a match made in quick bread heaven.

Do you want more delicious Cake Recipes?

This Yellow Cake with Chocolate Buttercream has everything you need to celebrate your next birthday!
Who would have thought this classic Homemade Pound Cake with cut strawberries and topped with whipped cream was so delicious?
I love this Banana Tres Leches Cake – an unbelievably moist banana cake topped with toasted coconut and sliced bananas.
Strawberry Poke Cake is an easy dessert perfect for Valentine’s Day or any day of the year. This basic white cake from scratch with homemade strawberry sauce and cream cheese frosting is so easy to make.
This ultra-decadent cake is a dream come true for any Oreo lover! It’s Oreo Cake with a surprise inside! It has layers of moist chocolate cake sandwiched with a cream filling, covered with a thick layer of homemade chocolate frosting, and stuffed with whole Oreos.
This easy Easy Tiramisu Poke Cake is the kind of cake that can be served for a casual get together or as a more sophisticated for an elegant dinner. The balance of coffee with the sweetness the cake and light icing is perfection.

When I did my original 365 days of baking, this Upside Down Pineapple Cake earned 3 ½ rolling pins. I used to rate everything I baked on a scale of 1-4 with 4 being the best. I LOVED it and it’s been added to my list of keepers!

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Created by: Lynne Feifer