If you’re looking for a dessert that conjures wonderful memories of days gone by, as well as being incredibly delicious. You’ve come to the right place.
This cake is a wonderful yellow butter cake topped with an amazing caramel sauce, pineapples, and cherries. It’s as beautiful in presentation as it is in incredible taste.
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HOW TO MAKE A CLASSIC PINEAPPLE UPSIDE-DOWN CAKE
This cake is truly not difficult to eat. We start by making a simple caramel sauce for the bottom of the pan (which will eventually be the top of the cake)!
Add the pineapple slices, cherries, and then the batter…and bake to perfection!
Watch us show you how to make this classic cake! It’s easy and so much fun!
CANNED OR FRESH PINEAPPLES
You know us, we always encourage you to use the freshest ingredients, and by all means, using fresh pineapple is great. But, we’ve tried it both ways, and fresh can be a bit problematic…there is a lot of water that is released that compromises the cake.
There are adjustments that can be made if you decide to cut up a fresh pineapple, but honestly, getting good quality, canned sliced pineapple, in pineapple juice, yields a wonderful cake, too. (Shhh..maybe even better!).
EXPERT TIP: This classic cake is often made in a 10-inch cast-iron skillet. It’s perfect for melting the butter and then pouring the batter and baking. We find once it’s time to invert the cooked cake, however, it is a little challenging. We’ve tested both cast-iron skillets and a 9-inch round (2-inch tall) cake pan, and they both have excellent results. Only difference? The cake pan version is MUCH easier to invert and release the cake. But if you want to keep it old school, go for it! You’ll probably just need an extra pair of hands to help when it’s time to flip the cake.
PINEAPPLE UPSIDE-DOWN CAKE IS DELICIOUS AND IS BEAUTIFUL IN PRESENTATION
The batter for this produces a perfectly moist and flavorful cake for this amazing dessert.
As mentioned, this is a classic yellow butter cake. Which happens to be the perfect match for the gooey caramel and juicy pineapples.
EXPERT TIP: The batter for this cake is somewhat thick. Use a rubber spatula to help gently spread the batter over the pineapples. As the cake bakes, you may see some of the butter bubbling along the edges of the pan. This is okay and is good. It forms an unbelievably delicious, almost candy-like exterior to the edge of the cake that is sublime.
After 45 minutes of baking, the cake will have risen slightly and turned a golden brown.
You may seem a thin layer of butter shimmering on the surface of the cake, this is normal.
EXPERT TIP: Insert a toothpick into the cake once you have reached 45 minutes. If the toothpick comes out clean, with no wet batter stuck to it, the cake is ready. If there is wet better attached to the toothpick, then the cake needs to go back in for another 5 to 10 minutes.
PINEAPPLE UPSIDE-DOWN CAKE IS A CLASSIC AMERICAN DESSERT
The pineapple upside-down cake was extremely popular back in the 50s and 60s and has seen a major comeback in recent years.
But actually, the cake dates all the way back to the 1800s and the pineapple upside-down cake is just one of numerous classic American cakes that made their place in so many homes across the country. Learn about more about American Cakes Throughout History from PBS.
And lifting the pan away from the inverted cake will make you feel like a rock star in your own kitchen.
If you’re interested in making another incredible American classic dessert, go with one of our favorites: Carrot Cake.
But in the meantime, if you’re looking to impress with a truly delicious and gorgeous cake, you just gotta try this recipe. Serve by the slice and just watch them go!
EXPERT TIP: Though this cake is wonderful at room temperature, there is something extra special when served still warm from baking. Comfort dessert food at its best.
THIS CAKE IS NOT DIFFICULT TO PREPARE
You will be surprised at how easy it is to make this incredible Classic Pineapple Upside Down Cake from scratch.
Of course, you could go with a box variety…but why no go a little extra distance and make it completely homemade?
You and your loved ones will enjoy this so much, it will probably become part of your regular dessert recipe rotation. It’s that good!
Ready to impress with one of the best cakes of all time? Go for it!
And when you do, be sure to take a picture, post if on Instagram, and tag @howtofeedaloon and hashtag #howtofeedaloon!
Classic Pineapple Upside-Down Cake
Video
Equipment
- 9-inch cake pan with 2-inch side, or 9 or 10-inch cast-iron skillet
Ingredients
FOR THE PINEAPPLE TOPPING
- 6 tablespoon unsalted butter melted
- ⅔ cup light brown sugar
- 8 pineapple rings canned, or fresh
- Maraschino cherries
FOR THE CAKE
- 1¾ cups all-purpose flour sifted
- 1½ teaspoon baking powder
- ¼ teaspoon Kosher salt
- ¾ cup unsalted butter 1½ sticks, softened
- 1 cup sugar
- 2 large eggs
- ¼ cup pineapple juice
- 1 tablespoon vanilla extract
- ½ cup whole milk
Instructions
MAKE THE TOPPING
- Pour the melted butter into cake pan or skillet.
- Sprinkle the brown sugar over the melted butter and then top with the pineapple slices, then place cherries in the centers of the rings and in the open spaces.
MAKE THE CAKE
- Preheat the oven to 350°F.
- In a medium bowl, whisk together the flour, baking powder, and salt. Set aside.
- Using a stand mixer, or a hand mixer with a large bowl, cream the sugar with the butter, by mixing on medium until slightly fluffy and pale in color, about 3 to 4 minutes. Scraping down the sides of the bowl a couple of times.
- Whisk in the eggs, pineapple juice, and vanilla extract.
- With the mixer running, add half of the flour mixture, once incorporated, add half of the milk. Once incorporated repeat with remaining flour and then milk. Mix until fully combined. The batter will be somewhat thick.
- Use a spatula to help pour the batter into the prepared pan and gently spread over the pineapples and cherries.
- Bake for 45 minutes, or until a toothpick comes out clean when stuck into the center of the cake.
- Let rest for 10 minutes, and then invert the cake on top of a cake stand or serving plate.
- Slice and serve warm or at room temperature. Great with ice cream or whipped cream!
Notes
Nutrition
POST UPDATE: This recipe was originally published in June 2018, but was updated with improved tweaks to the recipe, with new tips, photography, and a fabulous new video in February 2020!
Jessica Rupe says
I made the recipe for a friend’s birthday. Did a few tweaks to it. First, instead of pineapple rings I used tidbits (more pineapple per bite). Second, my friend doesn’t like cherries so I used walnuts instead at her request. Third, instead of vanilla I used pineapple baking emulsion (find in Michaels or Hobby Lobby in the cake decorating and candy making aisle). I mixed 1 teaspoon into the brown sugar, 1 teaspoon into the dry ingredients, and 1 teaspoon into the juice. Finally, as my friend is lactose intolerant I mixed the pineapple juice with water (I don’t have lactose free dairy milk on hand, nor extra pineapple juice, which is what I would normally do), and I used vegetable oil in the cake batter instead of melted butter, although I did use dairy butter in the caramel. The result is the pineapple flavor really shines through in this fabulous cake!
Kris Longwell says
Hi Jessica! Yay! Sounds like you prepared the cake perfectly!!! You obviously a wonderful baker!! Thanks so much for sharing and for the wonderful review! That means so much to us! Please stay in touch!!! Best, Kris & Wesley
Jessica Rupe says
Thank you so much for your quick reply and the compliment on my baking skills. My friend loved the cake when I brought it to her yesterday. She was so excited to try it she didn’t want to wait until today to cut into it!
Dana says
This is a fantastic recipe!! Fine tender crumb. Absolutely perfect!
Kris Longwell says
Hi Dana! Awesome! So so glad you made the cake and had such great success with it! We love it, too! Thanks for sharing and for the wonderful review! Please stay in touch!!! Best, Kris & Wesley
Tresa says
Not sure what I did wrong. I followed the recipe to a T and it came out dense and super dry. The topping was great. The cake flavor was ok. Had to cook longer than specified as cake was still sticking to the knife test.
Kris Longwell says
Hi Tresa, first…sorry for the delayed reply. Second…we’re sorry you didn’t have success with the cake! I wish I could tell you what went wrong! We make this cake several times a month, and as you can see from the comments, many home cooks have made it, too, with good results. Hard to know!!! Sometimes can come down to something as simple as weather, the pan you cooked it in, or ?? Thanks for letting us know and good luck in the new year!!! Kris & Wesley
Sherry Hill says
This cake was dang amazing. I hate it when people leave reviews and tell how they changed a recipe. BUT … it’s New Years Day and I only had chunk pineapple and self rising flour. It was perfect. Wasn’t as pretty as with ring pineapple, but didn’t affect the taste.
I put mine in a springform pan. I’m glad I put the pan on a cookie sheet lined with foil because that scrumptious brown sugar butter leaked just a tad.
Thank you gentlemen for this delicious cake recipe.
Kris Longwell says
Hi Sherry! Sounds like you prepared the cake perfectly!! Springform pans can be a little tricky, but you handled it like a pro!! Thank you so so much for sharing and for the wonderful review. That means so much to us. And…HAPPY NEW YEAR!!! Stay in touch! Kris & Wesley
Jackie says
This is just like the pineapple upside down cake my mom used to bake with me when I was little! I love baking this with my daughter, and the whole family loves eating it, too! Thanks for the great recipe!
Kris Longwell says
This makes us so happy, Jackie!! Thank you for letting us know!! Food memories are the BEST!!!!
Darla says
I was looking for a pineapple upside-down cake I could make from scratch to use a sugar substitute. I’m glad I found this one because it turned out fabulous! Now everyone in the house can eat this wonderful dessert.
Megan says
This is the best pineapple upside down cake I have ever made. It was fluffier and more tender than I expected, and I will absolutely make it again. I haven’t posted a review of a recipe in years, but I wanted to take the time to share how much I enjoyed this one in particular. Thanks!
Kris Longwell says
Megan! You just made our day! We are thrilled you made our upside-down pineapple cake and had such great success!! Thank you so much for sharing and for the wonderful review. That means the world to us! Please stay in touch! All the best, Kris & Wesley