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Easily the prettiest cake at the party, you just need a single standard 9-inch round cake pan to make this. My homemade Pineapple Upside Down Cake has easy-to-follow instructions, and soft cottony texture to the cake beneath the pineapple and cherries dripping in caramel syrup!

Yes this is the prettiest cake Iโve ever made! I donโt know why we donโt serve pineapple upside down cake at weddings! Everyone loves fruit, caramel, and a soft vanilla cake underneath!
This is the Best Pineapple Upside Down Cake
The benefits of making an upside down cake include:
-no need to make a frosting! The caramelized fruit is plenty of moisture on top of the vanilla cake!
-the beauty of the fruit arrangement. Itโs effortlessly visually stunning, without you having to do anything except fit 7 pineapple rings into the pan.
-the thrill when it plops out of the pan. It gives queen energy every time a cake pops out of the pan without sticking.
-the taste! Caramelized sugar, tangy pineapple, and sweet bright cherries are the best flavor combination!

Upside Down Pineapple Cake Ingredients

- Butter. This cake recipe needs one stick of butter for the cake and another half-stick to make the caramel topping that the fruit cooks in. For the cake, itโs best if the butter is completely softened to room temperature. Weโll use the other half a stick to melt with the brown sugar to make the caramel sauce.
- Brown Sugar. One-half cup of light brown sugar for making the caramel topping.
- Vanilla. One-quarter teaspoon of vanilla extract to flavor the caramel and another 1/2 teaspoon to flavor the cake batter.
- Pineapple. Itโs best to buy the 8-ounce can of pineapple rings packed in 100% pineapple juice. Weโll use 7 rings for making the design on the top of the cake. We also need 1/2 cup of pineapple juice from the can, so do not drain the can!
- Cherries. While bright red maraschino cherries are the most common thing to place in the center of each pineapple ring, I have also used Amarena cherries that I have from making cocktails with, and Iโve even used pecans instead of cherries! I think that might be a Texas thing to use pecans instead of cherries, though!
- Flour. One and a half cups of all-purpose flour for the cake batter.
- Baking Powder. One teaspoon of baking powder for making the cake rise.
- Granulated Sugar. One cup of white granulated sugar for the cake.
- Eggs. Two large eggs.

How to make Upside Down Pineapple Cake
Preheat the oven to 350-degrees F, and spray a 9-inch round cake pan generously with cooking spray. If youโre worried, you can line the bottom of the cake pan with a parchment paper round, but itโs not necessary. As long as you tip this cake out of the pan while itโs still warm, it will not stick to the pan!


First, make the topping (which goes in the bottom of the pan first). In a small saucepan, combine the 4 tablespoons of butter and brown sugar. Melt over low heat while stirring occasionally until smooth. Turn off the heat and stir in the vanilla.
Scrape the butter-brown sugar mixture into the bottom of the prepared cake pan.


Arrange as many pineapple rings in a single layer on top of the butter-brown sugar. Place a maraschino cherry in the center of each ring.
Next, make the cake: in a small bowl, whisk together the flour, baking powder, and salt. Set aside.


In a medium bowl, add the softened butter and granulated sugar. Beat with an electric mixer until smooth and fluffy, at least 1 minute. Add the eggs, vanilla, and pineapple juice and beat to combine.
Sprinkle the flour mixture on top, and beat just to combine. Scrape this mixture into the cake pan on top of the pineapple rings.


Bake for 45 minutes. To test for doneness, insert a toothpick just into the top layer of the cake (try to avoid the fruit). if the toothpick just has a few crumbs, itโs done. It should also start to pull away from the sides of the pan.
Let the cake cool in the pan for about 15 minutes, run a knife around the edge to loosen the sides, and then place a plate on top. Flip the cake over onto the plate, tap firmly to release.
Serving and Storage:
Personally, I like to slice this cake with a very sharp serrated knife so that it cuts through the pineapple slices cleanly. I like to serve it slightly warm with a scoop of vanilla ice cream or caramel gelato on top. You can serve it room temperature or cold, if thatโs how you prefer cake.

Tips for the Best Pineapple Upside Down Cake
- Caramel Topping โ Weโre not actually making caramel sauce here, so thereโs no need to worry about the proper temperature. Just melt the butter and stir in the sugar until itโs dissolved. Donโt let it boil or simmer too much because the water will evaporate from the butter and youโll have less liquid.
- Flipping the Cake โ This cake will not stick to the pan as long as you flip it when itโs still warm! if it does stick, itโs because the butter solidified, so put it back in a warm oven for a few minutes to melt the butter again. Itโs normal if a piece of fruit or two sticks, just lift it off and place it back where it belongs on the finished cake.
- Servings โ If you want a smaller batch of this cake, I made two Mini Pineapple Upside Down Cakes in ramekins a few years ago.
Upside Down Pineapple Cake FAQs
I let this cake sit on the counter for 1 day before I move it to the fridge for longer storage. You can also slice individually pieces, place them on a small paper plate, cover with two layers of plastic wrap and store in freezer-safe food bags. Then, you can defrost at room temperature anytime you need a single slice of cake!
If pineapple cake is soggy, itโs because it wasnโt baked long enough. Also, be sure to follow the instructions exactly and do not add any extra caramel sauce or pineapple juice to the recipe.
We like to eat it warm with a scoop of caramel gelato or vanilla ice cream, but you can eat it cold if you prefer! The caramel will be a little more firm if you eat it cold, though.
Pineapple Upside Down Cake from Scratch
Perfect pineapple upside down cake in a 9-inch pan!
Ingredients
FOR THE TOPPING:
- Cooking spray
- 4 tablespoons unsalted butter
- 1/2 cup light brown sugar
- 1/4 teaspoon vanilla extract
- 1 8-ounce can of pineapple rings in 100% pineapple juice
- 8 maraschino cherries
FOR THE CAKE:
- 1 1/2 cups all-purpose flour
- 1 teaspoon baking powder
- 1/2 teaspoon salt
- 8 tablespoons unsalted butter, softened to room temperature
- 1 cup sugar
- 2 large eggs
- 1/2 teaspoon vanilla extract
- 1/2 cup pineapple juice (from can)
Instructions
- Preheat the oven to 350-degrees F, and spray a 9-inch round cake pan generously with cooking spray.
- First: make the topping: In a small saucepan, combine the 4 tablespoons of butter and brown sugar. Melt over low heat while stirring occasionally until smooth. Turn off the heat and stir in the vanilla. Scrape this mixture into the bottom of the prepared cake pan.
- Arrange as many pineapple rings in a single layer on top of the butter-brown sugar. Place a maraschino cherry in the center of each ring. Set aside.
- Next, make the cake: in a small bowl, whisk together the flour, baking powder, and salt. Set aside.
- Then, In a separate medium bowl, add the softened butter and granulated sugar. Beat with an electric mixer until smooth and fluffy, at least 1 minute.
- Add the eggs, vanilla, and pineapple juice and beat to combine.
- Sprinkle the flour mixture on top, and beat just to combine.
- Gently scrape the batter on top of the pineapple rings, smooth the top, and bake for 45 minutes. Test after 45 minutes using a toothpick that you only insert in the top layer of the cake. Try not to get the fruit layer, which will be wet. The cake is done when the toothpick is mostly clean and the cake is starting to pull away from the sides of the pan.
- Let the cake cool in the pan for about 20 minutes, place a plate on top, and invert the pan over the plate. Tap down very firmly to help the cake release from the pan. If it doesnโt release, itโs because the butter solidified, so place it back in the oven for a few minutes and try again.
Notes
Nutrition Information:
Yield:
8Serving Size:
1Amount Per Serving: Calories: 445Total Fat: 19gSaturated Fat: 11gTrans Fat: 0gUnsaturated Fat: 7gCholesterol: 92mgSodium: 219mgCarbohydrates: 66gFiber: 1gSugar: 46gProtein: 5g














I donโt have the right size ramekins to do the smaller version, but do you think I could halve this one and do it in the 6 inch pan I use for all your other small cake recipes?
Hi there! I havenโt tested that. I made a big version in a 9-inch cake pan and a smaller version in mini ramekins. I donโt know that I have it in me to test another method LOL
That makes sense! If I get brave enough to try it myself, Iโll let you know if it worked!
Hi Christina,
Did you use a 9ร3 or a 9ร4 inch round cake pan for this upside down pineapple cake?
Thank you, Alina
The 9ร3 is the standard size. I believe the 9ร4 would be labeled โdeep dish.โ
I made this and it was delicious! One problem however is that the 8 oz can of pineapple rings only had 4 rings and the juice did not equal 1/2 cup. Luckily I had a can of pineapple bits in my pantry. Other than that, I am very pleased with this recipe and will make it again for hubby and I.
Oh no! I wonder if the brand you used sliced super thick slices because my 8-ounce cans always have 2 extra rings. If you didnโt have an extra can, I would have said to try to slice the thick slices, but Iโm glad t worked out :)