How to Make Retro Pineapple Upside Down Cake

When was the last time you enjoyed a slice of pineapple upside down cake? Be honest, it’s probably been a while. Since its heyday in the 1950s, this classic American cake’s appeal may have tapered off, but we believe it to be a dessert that never goes out of style. When made well, it’s nostalgically sweet—acceptably teetering the edge of cloying—glammed and glossy, just begging for a scoop of vanilla ice cream. 

The cake’s popularity may have peaked midcentury, but it actually started growing in household fame back in the 1920s. Recipes for it were popping up in newspapers such as the Boston Globe as far back as 1925. In the same year, James Drummond Dole’s Hawaiian Pineapple Company (now food giant Dole), in efforts to market canned pineapple to the American public, sponsored a contest for pineapple recipes. About 2,500 of the 60,000 submissions were for pineapple upside down cake. Since 2,500 upside down cake recipes were submitted, it's obvious the concept wasn’t new. But the contest followed by advertisements featuring the cake certainly gave the recipe widespread publicity. Recipes continued to pop up in newspapers and cookbooks until it was a dinner party staple in most US households. 

Those early versions were pretty much what you’ll often find today: Butter and sugar are first melted together to form a light caramel coating on the bottom of the pan, the fruit is then artfully fanned over the glaze, and the cake batter poured on top. After baking, you turn the pan over to reveal lacquered pineapple rings studded with requisite ruby-red maraschino cherries above a sturdy but tender cake. It’s retro dining at its finest.

The process of making pineapple upside down cake (or really any upside down cake) is fairly simple,  but to ensure that the cake is sweet with perfectly caramelized edges, well built, and releases from the pan easily in one-fell swoop, there are a few techniques to get right. We asked our Birmingham-based test kitchen colleague Marianne Williams to methodically flip cake after cake until she perfected the process. Here’s what we learned about how to bake a perfect pineapple upside down cake.

Tips for Baking a Pineapple Upside Down Cake

Stick with canned pineapple. There is a time and place for using fresh fruit in desserts; seasonal berry cobbler, peach pie, an apple tart. But a pineapple upside down cake is not one of them. Beyond the more abstract concept of canned pineapple “just feels right” in this dessert, perfectly portioned pineapple rings come out of the can already tender, glossy, sweet, and ready to go. Why fight it? 

In testing we found that cakes made with fresh pineapple not only required more work—cutting, portioning, cooking the fruit—but the pineapple flavor actually tasted less concentrated, and the fresh acidity distracted from the cake's sweet caramelized syrup on top.

Add pineapple juice, coconut oil, and rum to the cake. We wanted a cake where the pineapple flavor wasn’t just limited to the topping, but also echoed through the entire cake. To achieve this we used the pineapple juice from the can and cooked it down to concentrate its flavor before whisking it into the cake batter.

Unrefined coconut oil, which has a faint tropical coconut flavor, is also added to compliment the pineapple. While we initially tested the cake using all butter, we found that the rich, coconut-y flavor of unrefined coconut oil worked really well in the cake. (Make sure to use unrefined coconut oil, as refined coconut oil will lack coconut flavor.)

And we suggest leaning even further into the piña colada vibe with a splash of spiced dark rum in the batter. If you prefer not to use the rum, you can always omit it and instead add one tablespoon of water to the batter in its place.

Keep it simple and whisk the batter by hand. For a cake that is built on the ease of using canned fruit, we made sure there is no need to pull out a stand mixer or food processor for making the batter. In our testing, we found that hand-whisking was not only easier, but it also minimized the risk of over-aerating the batter, which would lighten and tenderize the cake too much.

When a cake batter is made in a stand mixer, the process involves creaming and lightening butter with sugar before vigorously whipping the batter. The goal of this is to incorporate as much air as possible to help lighten and tenderize the cake. This is great if your goal is a delicate, fluffy cake, but here we needed a sturdier cake that the syrupy glaze could soak into and still support the pineapple topping once flipped. We always like when easier also equals better.

Bake in a cast iron skillet. In testing, we found that baking in a cast iron skillet works wonders to create a more deeply caramelized pineapple layer with golden cake edges when compared to cakes baked in a standard cake pan. This is due to cast iron’s superior heat retention. Another perk of baking directly in the skillet is that you can melt the butter and build the syrup base in the same skillet you will bake in, avoiding an extra pan to clean later.

Cool the cake briefly before flipping it. Cooling the cake for about 15 minutes and then inverting it while it's still warm guarantees an easy release, but don’t let the cake cool in the skillet any longer than that before flipping. You don’t want the caramel to cool, firm, and stick to the bottom of the skillet. 

Our final advice for making sure the topping releases from the pan once flipped is to just be confident with your flip. Use oven mitts and use the handle to guide and flip the cake in one swift, steady motion. If a few pieces of pineapple or cherries remain stuck to the pan that is totally fine—just use a fork to gently lift them off and rearrange them on top of the cake. No one will even know.