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This Pineapple Upside Down Cake a delicious, classic cake that’s so easy to make. Fluffy cake layered with juicy pineapple and cherries create a retro dessert that’s simple yet satisfying.
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There’s a reason why Pineapple Upside Down Cake has remained a dessert staple for generations: it’s delicious! The sweet and tangy flavors are a perfect combination, while the fluffy cake topped with caramelized pineapple gives the treat lots of tasty textures. It’s been a favorite dessert for years; in fact, this dessert always reminds me of my grandmother’s dining table on warm Sunday afternoons as we all gathered for weekend meals. And while there’s been many variations over the years, you just can’t beat the classic recipe. If you’ve never made a pineapple upside down cake, this is one recipe you need to add to your collection.
Simple Steps to Pineapple Upside Down Cake
While the end product may look complicated and tricky, this is actually a very simple pineapple upside down cake recipe. All you need are a few pantry staples, a handy mixer and you’ll soon have a fluffy cake batter with gorgeous pineapple rings and cherries on top. It’s one of my favorite cakes to bake for company. Here’s all you need to do:
- First, grease a 9×3 round cake pan. A lot of recipes call for using a cast iron skillet, but I find a regular cake pan works just as well. I like to use baking spray, but you can use butter or oil and a sprinkle of all purpose flour. Set it aside, while you preheat your oven to 350 degrees.
- Next comes the base layer, this will end up being the top of your upside down cake. It’s an easy combination of one cup dark brown sugar and butter. Whisk that together in a saucepan over low to medium heat until smooth. I like to heat it until it has a creamy caramel color. Pour the sugar mixture into the bottom of the cake pan.
- Then, add pineapple rings and maraschino cherries. I don’t like a lot of extra pineapple juice in this layer, so I lightly pat the pineapple dry and place slices evenly over the top of the caramel mixture. Same goes with the cherries. Remove the stems, and dab them with a paper towel and place cherry in the center of each pineapple slice.
- Next, start on your homemade vanilla cake batter. In a medium sized bowl, sift together the dry ingredients of flour, salt, and baking powder, and then set aside.
- Here’s where I grab my handy mixer. You can use a hand held or a stand mixer. Combine white and dark brown sugar, melted butter, oil, whole eggs, and vanilla extract. I like to whisk it until the mixture is slightly fluffy.
- Grab the flour mixture that you set aside earlier, and add it a little at a time, alternating with stirring in a little whole milk. It needs to be just combined; be careful to not overmix.
- Pour the fluffy vanilla cake batter gently and evenly over the pineapple until the batter is evenly distributed throughout the pan. I like to get out every bit of that yummy batter with a rubber scraper. If you lick the scraper once you’re done, I won’t tell anybody!
- Pop the cake into the oven and bake for around 40 minutes. To check the doneness, I like to use a longer wooden skewer instead of a toothpick. You can find them next to the toothpicks in your grocery store. If the skewer comes out clean, the cake is done! If there’s a little batter on the skewer still, bake for another five minutes and check again.
- When it’s completely done, take the cake out of the oven. I recommend letting the cake rest for at least 10 minutes. Place a serving platter or cake plate over the top of the pan.
- Here’s where the magic happens. Turn the cake upside-down and carefully flip the cake out onto the plate. I use hot pads to invert the cake, because the pan should still be warm. Serve the cake warm with a scoop of ice cream or homemade whipped cream. The cream will melt right into the brown sugar topping. Perfection!
Recipe information
Classic pineapple upside-down cake has been around for generations, likely made popular when fruit canning became more streamlined. In the late 1930s and early 40s canning technology advanced, so companies could offer canned pineapple rings to people all over the country. Naturally, home cooks found a way to add it to desserts and the easy pineapple upside-down cake was born. It’s a staple at many family dinner tables and it still a popular dessert years later.
I love this easy homemade recipe. It doesn’t take long to make and it tastes so much better than the boxed version. Betty Crocker and other brands offer a decent version, but I promise taking a couple of extra steps will lead to a homemade cake with a rich, buttery texture and delicious tropical flavor.
Variations and Substitutions
- If you want your cake to be a little more dense, you can add a dollop of sour cream to the cake batter. You won’t taste it at all and the sour cream gives the cake extra moisture.
- Top the cake with a big scoop of vanilla ice cream or homemade whipped topping and add an extra maraschino cherry as a garnish.
- For extra texture and flavor, add a few chopped pecans or walnuts to the caramel layer. Sprinkle the nuts on before you layer the pineapple rings and cherries.
- If you’re still not sold on the idea of pineapple on a cake, you can switch up the fruit layer for anything you like! Try sliced fresh peaches, thinly sliced apples or just a jar of cherries. Each fruit will give the cake completely different flavors, so really it’s like you’re getting several cake recipes in one!
Recipe Tips
- Nothing is worse in my opinion than a soggy cake. I always pat the pineapple and cherries dry before adding them to the bottom of the cake pan to avoid getting too much moisture in the cake.
- Ovens all vary in their temperature and baking, so to ensure even baking you can loosely place foil over the top of the cake for the last 15 minutes of baking. That way it won’t get too brown on top and undone in the middle.
- Allow the cake to cool for 10-15 minutes before using hot pads to flip the cake over onto a serving platter.
- I love to serve this cake warm right out of the oven with a giant scoop of vanilla ice cream. It’s also delicious at room temperature the next morning for breakfast.
- Store leftovers in an airtight container either in the refrigerator or at room temperature for up to three days.
Pineapple Upside Down Cake with Cake Mix
If you’re in a hurry and need to get a dessert done quickly, you can always opt for using a yellow cake mix or vanilla cake mix instead of the homemade cake batter in the recipe. All you need to do is make the cake as directed on the box, using vegetable oil, water and eggs. Then continue the recipe below. It’s an easy switch that can save a little time in the kitchen.
Frequently Asked Questions
Yes of course! When using fresh pineapple I like to use a pineapple corer/slicer to get even rings and so they fit nicely in the cake pan.
I like to flip the cake within 10-20 minutes of the cake being removed from the oven. You want it to still be plenty warm when it is flipped.
No. Parchment paper isn’t necessary. I have found that just spraying the pan with cooking spray and then layering with the glaze will prevent the cake from sticking. You can always opt to add it if you are worried about it though!
Read Next: 33+ Easy Dessert Ideas
More Tropical Cake Recipes
I love these fresh, tropical cake flavors, especially during the hotter months. From juicy guava to pineapple to fresh coconut, try some of these tasty treats at your next summer supper.
Pineapple Upside Down Cake
Equipment
- 1 9"x3" cake pan
Ingredients
- 2 cups cake flour
- ½ teaspoon salt
- 2 teaspoons baking powder
- ¾ cup sugar
- ¼ cup dark brown sugar
- ½ cup butter melted
- ¼ cup canola oil or vegetable oil
- 3 eggs
- 2 egg yolks
- 2 teaspoons vanilla
- 1 cup milk
Topping
- ½ cup butter melted
- 1 cup dark brown sugar
- 7 pineapple slices (either fresh pineapple cored and sliced or you can use canned pineapple slices, it will be more uniform and look prettier– just make sure to pat it really dry)
- 7 Maraschino cherries
Instructions
- Preheat oven to 350-degrees. Prepare a 9"x3" round cake pan by spraying with cooking oil around the bottom and sides.
- In a saucepan, combine sugar and butter and heat over low medium heat until smooth and a light caramel color. Pour evenly into the bottom of the prepared pan. (if you like the cake really gooey and caramel-y you can double the butter/brown sugar mixture)
- Pat pineapple dry and place slices evenly over the top of the caramel mixture. Pat cherries dry and place in the middle of each pineapple ring.
- In a medium sized bowl, sift together flour, salt, and baking powder, set aside.
- In a large mixing bowl combine sugars, melted butter, oil, eggs, egg yolks, and vanilla and mix well.
- Add flour mixture and milk a little at a time, alternating between the two. Do not over mix.
- Pour batter gently and evenly over the pineapple until the batter is evenly distributed throughout the pan.
- Bake for 40 minutes on the middle rack of the oven. After 40 minutes check for doneness with a wooden skewer. Place the skewer through the middle of the cake, if it comes out clean it's done. If needed, bake for 5 minutes more at a time, checking for doneness until the cake is done.
- When the cake is done, remove from the oven. Allow cake to rest for 10-15 minutes. Place a serving plate over the top of the pan.
- Using hot pads if pan is still hot, carefully flip the cake out onto the plate while it is still quite warm.
- Serve warm.
