Pineapple Upside-Down Cake Is the Retro Dessert That's Always a Star (2024)

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Meghan Splawn

Meghan was the Food Editor for Kitchn's Skills content. She's a master of everyday baking, family cooking, and harnessing good light. Meghan approaches food with an eye towards budgeting — both time and money — and having fun. Meghan has a baking and pastry degree, and spent the first 10 years of her career as part of Alton Brown's culinary team. She co-hosts a weekly podcast about food and family called Didn't I Just Feed You.

Jan Valdez

Jan ValdezAssistant Recipe Producer at The Kitchn

I got into this field by spending 10 years working in Research & Development and Product Development test kitchens, testing new products and recipes. For nearly eight years, I was the Senior Culinary R&D Specialist at Weber headquarters, where all the grills are designed, engineered, and tested. I've helped launch numerous best-selling, top-rated grills across the globe (you should see my grill collection at home!).One of my proudest accomplishments happened years earlier, when I had the opportunity to visit the Good Housekeeping Institue in NYC after developing an award-winning Tropical Citrus Shrimp recipe that jumpstarted my career in test kitchens and food editing. Since then, I've worked at Serious Eats (one of my favorite food sites) and EatingWell as an updates editor.I'm passionate about both classic recipes and new, unique twists. I'm constantly learning and that's what makes food and cooking so fun (just ask me how to bake light and airy pavlovas on the grill – I've tested them countless times!).

updated Mar 26, 2024

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Pineapple Upside-Down Cake Is the Retro Dessert That's Always a Star (1)

A classic cake for good reason, this rich, buttery cake topped with fragrant, caramelized pineapple and amber cherries is pantry-friendly and easy to make.

Serves8 to 10Makes1 (9-inch) cake

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Pineapple Upside-Down Cake Is the Retro Dessert That's Always a Star (2)

It is hard to overstate how simple yet stunning pineapple upside-down cake is. This cake has retro charm, but it’s a classic whose appeal hasn’t waned since it first appeared on the home baking scene. It starts with a rich butter cake that, once removed from the pan, reveals a design of caramelized pineapple rings studded with maraschino cherries. Each bite is little treasure chest of flavor — tender cake, mingled with the sweet and slightly tangy notes of pineapple and cherry.

Tips for Making the Best Pineapple Upside-down Cake

Cook and cool the brown sugar topping before making the cake batter. Butter and light brown sugar make up the glaze that bakes at the bottom of this cake. It holds the pineapple and maraschino cherries in place once the cake has cooled. Do this step first before arranging the pineapple and cherries on top of the glaze.
Dollop, don’t pour the batter. The batter for this cake is quite thick! Avoid knocking the pineapple and topping around by scooping the batter into big dollops on top of the fruit and then gently spreading it out with a spatula.
Cool the cake slightly before removing from the pan. The hardest part of making pineapple upside-down cake is the maneuver which turns the bottom of the cake pan into the top of the cake. Cooling the baked cake slightly before flipping it allows the topping to cool and stick to the cake before turning out.

Why You’ll Love It

Pineapple upside-down cake has a near universal appeal — this single layer cake only requires one bowl to mix, and it isn’t overly sweet.
We’re also incorporating more pineapple flavor by using the pineapple juice in the cake batter! Because hello, the juice around those pineapple rings is sweet and full of flavor, so why waste it?

The History of Pineapple Upside-Down Cake

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 1925, but upside-down cakes have a history born before home ovens, when these “skillet cakes” were baked over a fire.

Pineapple upside-down cake’s popularity peaked in the 1950s (which is where it gets its retro reputation from), but it’s stuck around, becoming just as much of a classic because it’s so easy to make.

Key Ingredients in Pineapple Upside-Down Cake

Canned pineapple rings in pineapple juice: We prefer to keep with the classic canned pineapple rings, as they give the cake its iconic look. Make sure to reserve 1/2 cup of the pineapple juice for the cake batter. If you were to use fresh pineapple, keep in mind that it produces considerably more juice while cooking and might not have the same sticky-sweet topping as canned pineapple.
Sugar: You’ll need two types for this recipe: granulated sugar for the batter, andlight brown sugar for the sticky glazed topping.
Maraschino cherries: These sweet ruby-red gems give the cake its signature look.
All-purpose flour: Skip the cake flour — basic all-purpose flour works best for this classic cake.

How to Make Pineapple Upside-Down Cake

Make the topping. Melt the butter and sugar in a small pan over medium heat, stirring frequently, until the sugar is bubbly and slightly more brown. Pour the sugar mixture into aprepared cake pan and spread into an even layer to cool slightly.
Arrange the pineapple slices and cherries in the cake pan. Remove the pineapple rings from the can (reserving some of the juice!). Set a single ring in the center of the pan, then arrange 6 to 7 rings around the center ring. Place a maraschino cherry in the center of each ring and set the pan aside.
Make the batter. Whisk together the dry ingredients. Cream the butter and the sugar together, then beat in eggs. To the wet ingredients, add the flour mixture and pineapple juice in alternating batches.
Spread the batter over the fruit. Use a large spoon to dollop large spoonfuls of the batter evenly over the fruit in the pan. Smooth the batter with an offset spatula, then tap the cake pan lightly on the counter to settle the batter.
Bake the cake. Bake the cake until dark golden-brown and a cake tester comes out clean, about 45 minutes.
Cool the cake for 10 minutes and then invert the cake onto a serving plate. Invert a plate over the cake pan and, using kitchen towels or oven mitts to grasp onto both the plate and the cake pan, flip both the pan and the plate over so the pan now sits on top of the plate.

How to Flip Pineapple Upside-Down Cake Perfectly

Once your pineapple upside-down cake is baked and slightly cooled, you’ll need to flip the cake out onto a serving plate.

First, pick a low plate or cake stand.
Run an off-set spatula or thin butter knife between the cake and the pan.
Set the serving plate over the cake pan and flip the two together.
Now let gravity slowly drop the pineapple cake out of pan — banging or thrusting the pan may break the cake, so have a little patience here!
Finally, if any pineapples or cherries have slipped out of place, gently nudge them back where they belong.

More Upside-Down Cake Recipes You’ll Love

Storage Tips

Leftovers can be stored in an airtight container at room temperature for up to 3 days.

Comments

Pineapple Upside-Down Cake Recipe

A classic cake for good reason, this rich, buttery cake topped with fragrant, caramelized pineapple and amber cherries is pantry-friendly and easy to make.

Makes 1 (9-inch) cake

Serves 8 to 10

Nutritional Info

Ingredients

For the topping:

Cooking spray
4 tablespoons
unsalted butter
1/2 cup
packed light brown sugar
1 (8-ounce) can
pineapple rings in pineapple juice
8 to 10
maraschino cherries

For the cake:

1 1/2 cups
all-purpose flour
1 teaspoon
baking powder
1/4 teaspoon
salt
1 cup
granulated sugar
8 tablespoons
(1 stick) unsalted butter, at room temperature
2
large eggs

Instructions

Show Images

Arrange a rack in the middle of the oven and heat to 350°F. Coat a 9-inch round cake pan with cooking spray; set aside.
Melt 4 tablespoons unsalted butter and 1/2 cup packed light brown sugar in a small pan over medium heat, stirring frequently. The mixture is done when the sugar is bubbly and slightly more brown.
Pour the sugar mixture into a prepared cake pan and spread into an even layer to cool slightly.
Remove the pineapple rings from the can and reserve 1/2 cup of the juice. Set a single ring in the center of the pan, then arrange 6 to 7 rings around the center ring. Place a maraschino cherry in the center of each ring and set the pan aside.
Whisk 1 1/2 cups all-purpose flour, 1 teaspoon baking powder, and 1/4 teaspoon salt together in a medium bowl; set aside.
Place 1 cup granulated sugar and 8 tablespoons (1 stick) unsalted butter (at room temperature) in a large bowl. Using an electric hand mixer, beat on medium speed until lightened and creamy, about 5 minutes. Add 2 large eggs and beat until smooth, about 1 minute more.
With the mixer on low speed, add the flour mixture in 3 batches, alternating with the reserved 1/2 cup pineapple juice, in this order: Add 1/3 of the flour mixture and mix until incorporated, about 30 seconds. Add 1/2 of the pineapple juice, mixing until smooth, about 30 seconds. Add another 1/2 of the remaining flour and mix again for about 30 seconds, followed by the remaining pineapple juice and 30 seconds of mixing. Finally, add the remaining flour mixture and mix until completely smooth, about 1 minute total.
The batter will be thick, so use a large spoon to dollop large spoonfuls of the batter evenly over the fruit in the pan. Smooth the batter with an offset spatula, then tap the cake pan lightly on the counter to settle the batter.
Bake the cake until dark golden-brown and a cake tester comes out clean, about 45 minutes.
Remove the warm cake from the oven to a cooling rack and cool for 10 minutes (do not wait longer or the cake will not come out of the pan). Invert a plate over the cake pan and, using kitchen towels or oven mitts to grasp onto both the plate and the cake pan, flip both the pan and the plate over so the pan now sits on top of the plate. Slowly lift the cake pan away. Serve the cake warm or cool before serving and storing.

Recipe Notes

Storage: Leftovers can be stored in an airtight container at room temperature for up to 3 days.

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