Pineapple Upside Down Cake
An Old-Fashioned Pineapple Upside Down Cake is a retro classic that will simply never goes out of style.
A layer of buttery brown sugar caramelizes under sweet pineapple rings and bright maraschino cherries, all topped with a soft, tender vanilla cake.
The best part? It flips right out of the pan to reveal its signature golden topping—no frosting needed.
With simple ingredients and a straightforward method, this cake is perfect for any occasion, from family dinners to holiday gatherings. If you’ve never made one from scratch before, don’t worry—we’re walking you through every step to make sure it turns out beautifully.
Pineapple Upside Down Cake Recipe Highlights
- Just 10 minutes of prep and the oven does the rest with no complicated techniques required
- Flips out like magic revealing a golden caramelized pineapple topping that needs no frosting
- Moist buttery and full of flavor thanks to a simple batter made from scratch
- Foolproof for any level of baker with no tricky layers or decorating needed
- Perfect for any occasion from family dinners to holiday gatherings because retro desserts never go out of style
Ingredient Notes
Please check the recipe card below for a detailed, printable ingredient list.
SUGAR – This recipe uses brown sugar and granulated sugar, each serving a different role. Brown sugar melts into the butter to create the sticky caramelized topping, giving the cake its signature deep flavor and glossy finish. Light brown sugar provides a milder sweetness, while dark brown sugar adds a stronger molasses taste. Granulated sugar is used in the batter to create a light, balanced sweetness without weighing down the cake. Using all brown sugar would make the cake too sticky, while only granulated sugar wouldn’t develop the same rich topping.
PINEAPPLE – The topping features pineapple slices, while pineapple juice adds moisture and flavor to the cake. Canned pineapple in juice is the best option because the slices are uniform in size and the juice is naturally sweet without added sugar. Fresh pineapple can be used, but it must be sliced evenly and thoroughly patted dry to prevent excess moisture. The reserved pineapple juice from the can is blended into the cake batter, adding flavor and tenderness. Avoid using pineapple juice from concentrate, as it can be too strong and alter the cake’s texture.
CHERRIES – Maraschino cherries bring a bright pop of color and sweetness to the topping. They are soft and slightly chewy, complementing the caramelized pineapple. To prevent them from bleeding into the cake, pat them completely dry before placing them in the pan. If you prefer a more natural option, you can use fresh or frozen cherries, but they won’t have the same candy-like sweetness.
FLOUR AND LEAVENING AGENTS – All-purpose flour provides the cake’s structure while keeping it soft. To avoid a dense cake, spoon and level the flour rather than scooping it straight from the bag, which can pack it down and lead to too much flour. The combination of baking powder and baking soda helps the cake rise properly. Baking powder does most of the lifting, while baking soda reacts with the yogurt to create a tender, airy texture. Too much of either can throw off the cake’s balance, causing it to rise too quickly and collapse or develop a bitter aftertaste.
BUTTER – Unsalted butter is used in both the topping and the cake batter for richness and a smooth texture. In the topping, it combines with brown sugar to create a caramel-like layer that coats the pineapple and cherries. In the batter, it adds moisture while keeping the cake soft and tender. Use softened butter for the batter—if it’s too cold, it won’t mix properly, and if it’s too warm, the cake can turn greasy.
EGGS – Eggs help bind the batter and create structure. Room temperature eggs mix more evenly into the batter, giving the cake a smoother texture and helping it rise properly. If you need to bring eggs to room temperature quickly, place them in a bowl of warm water for five minutes before using.
YOGURT – Vanilla yogurt keeps the cake moist and gives it a slight tang that balances the sweetness. A full-fat vanilla yogurt works best for a rich texture, but plain yogurt or sour cream can be substituted. Avoid using nonfat yogurt, as it can make the cake drier. Greek yogurt can work, but it’s thicker, so you may need to thin it with a splash of pineapple juice.
EXTRACTS – A mix of vanilla extract and almond extract gives the cake its warm, fragrant flavor. Vanilla adds depth, while almond extract enhances the tropical notes of the pineapple. If you prefer a more traditional flavor, you can skip the almond extract, but even a small amount makes a difference in rounding out the cake’s sweetness.
How To Make A Pineapple Upside Down Cake
Please check the printable recipe card below for more detailed instructions.
- Brush a 9-inch cake pan with butter, sprinkle brown sugar, and arrange pineapple slices and cherries.
- Beat butter and sugar, then mix in eggs, yogurt, pineapple juice, and extracts.
- Stir in flour, baking powder, baking soda, and salt until just combined.
- Pour batter over fruit and bake at 350º Fahrenheit for 25 minutes covered, then uncover and bake 20 more minutes.
- Cool for 20 minutes, flip onto a plate, and lift off the pan.
- Let cool completely before slicing.
Leftovers and Storage
STORE – Keep Pineapple Upside Down Cake covered tightly with plastic wrap or in an airtight container. It stays fresh at room temperature for up to 2 days, but for longer storage, refrigerate for up to 5 days—just know that chilling can make the cake firmer, so let it sit out for 30 minutes before serving.
FREEZE – For best results, freeze individual slices by wrapping them tightly in plastic wrap and placing them in an airtight container to prevent freezer burn. If freezing the whole cake, place parchment paper on top before wrapping it in plastic and foil. Thaw at room temperature for a few hours before serving to keep the topping intact.
REHEAT – Warm Pineapple Upside Down Cake in the microwave for 10-15 seconds for a quick option, but if you want to restore its freshly baked texture, heat it in a 300º Fahrenheit oven for 5-7 minutes. Avoid overheating or the caramelized topping may turn sticky and runny.
MAKE AHEAD – Bake Pineapple Upside Down Cake a day ahead, but do not flip it immediately if storing overnight—leave it in the pan, covered in plastic wrap, and refrigerate. Before serving, bring it to room temperature, then flip it onto a plate to prevent the caramelized topping from sticking.
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Serving Suggestions
WHIPPED CREAM – The light, airy texture of the Pineapple Upside Down Cake works beautifully with the warm, caramelized topping. For the best pairing, whip fresh cream with a touch of vanilla.
VANILLA ICE CREAM – A scoop of cold, creamy ice cream melting over a slice of warm cake is pure magic. For an extra flavor boost, try French vanilla or even coconut ice cream.
TOASTED COCONUT – A light sprinkle of toasted shredded coconut adds a bit of crunch and enhances the tropical flavors. If you want an even deeper flavor, toast the coconut in a dry pan until golden brown before adding it to the cake.
CARAMEL SAUCE – A warm drizzle of caramel sauce makes the buttery pineapple topping even more indulgent. For a quick upgrade, sprinkle a little sea salt over the caramel before serving.
ESPRESSO OR COFFEE – The bold, slightly bitter notes of a hot cup of coffee balance out the cake’s sweetness perfectly. A dark roast or espresso works best to complement the deep caramel flavors in the topping.
Recipe Success Tips
PAT THE PINEAPPLE AND CHERRIES DRY – Extra moisture can make the topping too wet and prevent proper caramelization. Use a paper towel to blot the fruit before placing it in the pan for the best texture.
SPREAD THE BATTER GENTLY – The fruit layer is delicate, so spoon the batter over the top rather than pouring it all at once. Lightly spread it with a spatula to avoid shifting the pineapple and cherries.
BAKE COVERED FOR EVEN COOKING – Tent the cake with foil for the first 25 minutes to prevent the top from over-browning before the center bakes through. Removing the foil at the right time ensures a golden, even finish.
COOL BEFORE FLIPPING, BUT NOT TOO LONG – Let the cake rest for 20 minutes before flipping to prevent it from falling apart. Waiting too long can make the caramelized sugar harden, making it more likely to stick to the pan.
RUN A KNIFE AROUND THE EDGE BEFORE FLIPPING – This helps loosen the cake and keeps the fruit topping intact. A gentle tap on the pan before lifting it away ensures a clean release.
Commonly Asked Questions
Can I use fresh pineapple instead of canned?
Yes, fresh pineapple works, but it must be sliced evenly and patted completely dry to prevent excess moisture from making the cake soggy. Canned pineapple is preferred because it’s consistently sweet and already cut to the perfect thickness.
Why did my Pineapple Upside Down Cake stick to the pan?
If the cake sticks, it may not have cooled long enough before flipping or there wasn’t enough butter in the topping. Let it rest for 20 minutes, then run a knife around the edges before inverting it onto a plate.
How do I prevent my cake from becoming too dense?
Make sure to measure the flour correctly by spooning it into the measuring cup and leveling it off. Overmixing the batter can also make the cake dense, so stir just until the ingredients are combined.
More Easy and Delicious Desserts
Pineapple Upside Down Cake
Ingredients
Topping
- 4 tablespoons unsalted butter melted
- ½ cup brown sugar packed
- 1 20-ounce can pineapple slices in juice, reserve juice
- 1 10-ounce jar maraschino cherries
Cake Batter
- 1 ½ cups all-purpose flour
- 1 teaspoon baking powder
- ¼ teaspoon baking soda
- ¼ teaspoon salt
- 8 tablespoons unsalted butter softened
- ¾ cup granulated sugar
- 3 large eggs room temperature
- ⅓ cup vanilla yogurt
- 6 tablespoons pineapple juice reserved from the can
- 1 teaspoon vanilla extract
- ¼ teaspoon almond extract
Instructions
Prep
- Preheat the oven to 350°Fahrenheit.
- Brush a 9” round cake pan (at least 2” high) with 4 tablespoons melted butter. Coat the bottom and the sides with butter. Sprinkle the brown sugar over the melted butter to coat the bottom of the pan.
Pineapple Top Layer
- Pat the pineapple slices and maraschino cherries dry with paper towels. Arrange the pineapple slices in the bottom and sides of the cake pan.
- Arrange the cherries inside and around the pineapple slices. Gently press the fruit into the pan and let it set in the refrigerator while mixing the batter.
Cake Batter
- Mix the flour, baking powder, baking soda, and salt in a medium bowl. Set aside.
- Beat the softened butter and sugar in a large bowl with a mixer on high, until fluffy. Reduce the speed to medium and add the eggs, one at a time. Add the yogurt, reserved pineapple juice, vanilla extract, and almond extract to the bowl and continue to beat until just incorporated.
- Add the flour mixture to the wet ingredients and mix on medium speed, just until blended. Slowly pour the batter into the cake pan.
- Cover the cake pan with aluminum foil and bake for 25 minutes. Remove the foil and bake for another 20 minutes, or until the cake is baked through. Use a toothpick to check for doneness.
- Let the cake cool for 20 minutes. Cover the pan with a serving plate, then flip it over. Gently tap the pan all over and lift and remove it from the cake. Once the cake has cooled completely, serve and enjoy.
Equipment
Nutritional Information
Nutritional Disclaimer
Cheerful Cook team members are not trained nutritionists or medical professionals. Calorie information and nutritional values are estimates. If you have nutritional concerns, we recommend using a nutritional calculator.
Maike Corbett is the founder and food blogger of Cheerful Cook, a popular recipe website featuring comfort food recipes from the US and Germany. She has been featured in numerous media outlets, including the AP Wire and MSN.
Can I use a square or rectangular pan — and if so, what dimensions? Sounds delicious.
Great question. Yes, you can definitely use a square or rectangular pan! An 8×8-inch square pan or a 9×7-inch rectangular pan would work perfectly, as long as it’s at least 2 inches deep to match the volume of the original 9-inch round pan. You’ll just need to arrange the pineapple slices to fit the corners, and the baking time should remain the same at 45 minutes total. The caramelized topping will look beautiful in any shape!