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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!

Vertical image of pineapple upside down cake with cherries in center.

Yes this is the prettiest cake Iโ€™ve ever made! I donโ€™t know why we donโ€™t 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. Itโ€™s 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!

A slice of pineapple upside down cake on a plate with the tip missing.
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Upside Down Pineapple Cake Ingredients

Bowl with fruit rings, cherries, eggs, flour, butter and vanilla on kitchen counter.
  • 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, itโ€™s best if the butter is completely softened to room temperature. Weโ€™ll 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. Itโ€™s best to buy the 8-ounce can of pineapple rings packed in 100% pineapple juice. Weโ€™ll 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 Iโ€™ve 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.
Overhead image of pineapple upside down cake sliced.

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 youโ€™re worried, you can line the bottom of the cake pan with a parchment paper round, but itโ€™s not necessary. As long as you tip this cake out of the pan while itโ€™s still warm, it will not stick to the pan!

Small white saucepan with butter and brown sugar about to be melted.
Brown caramel sauce in the bottom of a round 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.

Seven pineapple rings with cherries in the center over brown caramel in a round cake pan.
White bowl with white powders in it with a whisk.

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.

Bowl with yellow butter, eggs and vanilla splashed on top.
Bowl with yellow cake batter and white flour on top, before being stirred in.

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.

Freshly baked yellow cake in a round cake pan.
A pineapple upside down cake flipped over on a white plate for serving.

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, itโ€™s 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 thatโ€™s how you prefer cake.

Close up of upside down pineapple cake toppings.

Tips for the Best Pineapple Upside Down Cake

  • Caramel Topping โ€“ Weโ€™re not actually making caramel sauce here, so thereโ€™s no need to worry about the proper temperature. Just melt the butter and stir in the sugar until itโ€™s dissolved. Donโ€™t let it boil or simmer too much because the water will evaporate from the butter and youโ€™ll have less liquid.
  • Flipping the Cake โ€“ This cake will not stick to the pan as long as you flip it when itโ€™s still warm! if it does stick, itโ€™s because the butter solidified, so put it back in a warm oven for a few minutes to melt the butter again. Itโ€™s 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

Does pineapple upside down cake need to be refrigerated?

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!

Why is my pineapple upside down cake soggy?

If pineapple cake is soggy, itโ€™s because it wasnโ€™t 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.

Do you eat pineapple upside down cake warm or cold?

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.

Yield: 8

Pineapple Upside Down Cake from Scratch

Vertical image of pineapple upside down cake with cherries in center.

Perfect pineapple upside down cake in a 9-inch pan!

Prep Time 15 minutes
Cook Time 50 minutes
Total Time 1 hour 5 minutes

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

  1. Preheat the oven to 350-degrees F, and spray a 9-inch round cake pan generously with cooking spray.
  2. 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.
  3. 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.
  4. Next, make the cake: in a small bowl, whisk together the flour, baking powder, and salt. Set aside.
  5. 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.
  6. Add the eggs, vanilla, and pineapple juice and beat to combine.
  7. Sprinkle the flour mixture on top, and beat just to combine.
  8. 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.
  9. 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 doesnโ€™t release, itโ€™s because the butter solidified, so place it back in the oven for a few minutes and try again.

Notes

Nutrition Information:

Yield:

8

Serving Size:

1

Amount Per Serving: Calories: 445Total Fat: 19gSaturated Fat: 11gTrans Fat: 0gUnsaturated Fat: 7gCholesterol: 92mgSodium: 219mgCarbohydrates: 66gFiber: 1gSugar: 46gProtein: 5g

Did you make this recipe?

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About Christina Lane

Christina Lane is the author of 5 cookbooks all about cooking and baking for two. She has scaled down hundreds of recipes into smaller servings so you can enjoy your favorite dishes without the leftovers! Valentine's Day is her favorite holiday.

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7 Comments

  1. Melina says:

    I donโ€™t 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?

    1. Christina Lane says:

      Hi there! I havenโ€™t tested that. I made a big version in a 9-inch cake pan and a smaller version in mini ramekins. I donโ€™t know that I have it in me to test another method LOL

      1. Melina says:

        That makes sense! If I get brave enough to try it myself, Iโ€™ll let you know if it worked!

      2. Alina says:

        Hi Christina,

        Did you use a 9ร—3 or a 9ร—4 inch round cake pan for this upside down pineapple cake?

        Thank you, Alina

        1. Christina Lane says:

          The 9ร—3 is the standard size. I believe the 9ร—4 would be labeled โ€˜deep dish.โ€™

  2. Sue Prior says:

    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.

    1. Christina Lane says:

      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 didnโ€™t have an extra can, I would have said to try to slice the thick slices, but Iโ€™m glad t worked out :)