Cakes, Recipes

Pineapple Upside Down Cake

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Pineapple Upside Down Cake
CAKES – MAY 5, 2023

Pineapple Upside Down Cake

This Pineapple Upside down Cake has sweet caramelized pineapple rings and maraschino cherries baked into a fluffy yellow vanilla cake and it is a family favorite that brings back joyful memories.

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This is a classic Pineapple Upside Down Cake. It has a layer of caramelized pineapple with maraschino cherries on top, with a soft buttery vanilla cake. The cake is baked with pineapples and cherries at the bottom of the pan and then inverted onto a plate, resulting in a gorgeous and stunning upside-down presentation. 

Everyone I talk to that has had this cake tells me that they have the most beautiful memories. It tends to be because their grandma, their parents, or a beloved friend made it for them for the first time once many years ago. Because of this, all I feel is warmth. Warmth for those memories that are evoked for “just cake”.

Pineapple Upside Down Cake

Why you will love this Pineapple Upside-Down Cake?

Where should we start? This cake is an absolute favorite (unless you despise pineapples). 

The first reason is its flavor. The combination of sweet and juicy pineapples with the tart flavor of the maraschino cherries is perfect with the soft and moist vanilla cake. Additionally, they add flavor to the cake while it is baking, giving you that delicious moist, and soft cake.

Secondly, the presentation is stunning and will impress your guests (or even yourself!). Besides, you get to play around with designs and can come up with super creative things like pineapple flowers, or maybe all rings.

Finally, this cake is incredibly easy to make and can be whipped up in no time at all.

Pineapple Upside Down Cake

Ingredients for Pineapple Upside Down Cake:

To begin with, the method I use in this cake may be controversial. Mixing all the cake ingredients together is something you may have not seen in a while if not ever. In fact, I get it. Mixing all the ingredients together for a long time may develop gluten and make your cake tough but not this one! I promise, somehow this works. Maybe it’s the steam from the pineapples when they bake, or the gooey caramel at the bottom. In short, it works and this cake is soft and moist every single time. 

To summarize, the most important advice I can give you is to have all the cold ingredients at room temperature before adding them in. Of course, that means extra soft butter, room-temperature eggs, and room-temperature milk. You will not regret the result of baking this beauty!

To make this pineapple upside-down cake, you will need the following ingredients:

For the pineapple base:

  • Canned pineapple rings: The pineapple rings are the star of this dessert and are what give it a deliciously sweet and tangy flavor. However, you can substitute with fresh thinly sliced pineapple.
  • Maraschino cherries: these add a pop of color and a tart flavor that balances out the sweetness of the pineapple. Any brand works like this one. But you can substitute with fresh cherries, pitted and halved, or leave them out entirely.
  • Brown sugar: The brown sugar is used to create a caramelized topping that pairs perfectly with the pineapple and cherries. Domino has great light brown sugar
  • Butter: creates the buttery caramelized topping. 

For the cake:

  • Butter: makes the cake soft and moist and creates the caramelized topping. Make sure it is at room temperature! Can substitute with vegetable oil.
  • All-purpose flour: used to give the cake structure and helps it rise during baking.
  • Granulated sugar: The sugar is used to sweeten the cake and create a tender crumb. 
  • Eggs: The eggs are used to bind the ingredients together and add moisture to the cake. Make sure it is at room temperature!
  • Milk: The milk is used to create a smooth and creamy batter. Make sure it is at room temperature! Can substitute for plant-based milk but the flavor may change a bit.
  • Pineapple juice: use from the can of pineapple rings. Adds a pineapple flavor hint to the cake.
  • Baking powder: The baking powder is used to help the cake rise and become fluffy.
  • Vanilla extract: The vanilla extract is used to add flavor and aroma to the cake.
  • Almond extract: the almond extract pairs well with the vanilla cake. It is optional but this is the one I like as I feel it doesn’t give that fake almond flavor.
Pineapple Upside Down Cake

Tips for making the best Pineapple Upside Down Cake

  1. Arrange the pineapple and cherries in a decorative pattern. However, this is totally up to you. With this recipe, you can use a square 8×8-inch pan or a 9-inch pan (this one is my favorite, nothing sticks!) and arrange your design in whichever pattern you prefer. Get creative with your design or simply place the pineapple rings in a neat circular pattern.
  2. Use room temperature ingredients: For the cake, it is extremely important that you use room temperature ingredients so that they mix well, especially with the method I use in this recipe.
  3. Use cake flour for a lighter cake: If your all-purpose flour has a high protein content, substitute for cake flour so you can achieve a light and tender cake.
  4. Let the cake cool before removing it from the pan: Once your cake is finished baking, let it cool in the pan on a wire rack for 10 minutes before removing it. It allows the cake to set and comes out easier. However, it is important to unmold it while it’s still hot and before the caramel sets and sticks to the bottom of the pan.
  5. Use a large plate to flip the cake: Place a plate over the top of the pan and quickly flip the pan over. The cake should release easily from the pan onto the plate. If fruit sticks to the pan, release it with a spatula and place it in your cake design.
  6. Serve the cake warm or at room temperature: Pineapple upside-down cake is best served warm or at room temperature. In fact, the cake and the caramelized topping can get too hard if eating it cold our of the fridge.
  7. More servings? Double the recipe: This recipe can be doubled confidently and baked into a 9×13’ pan.

Pineapple Upside Down Cake
Pineapple Upside Down Cake

Pineapple Upside Down Cake

Author: Seidy
This cake has sweet caramelized pineapple rings and maraschino cherries baked into a fluffy yellow vanilla cake and it is a family favorite that brings back joyful memories.
Prep Time 10 minutes
Cook Time 35 minutes
Cooling Time 10 minutes
Total Time 1 hour
Course Breakfast
Cuisine American
Servings 12 slices


For the Pineapple Base:

  • ¼ cup unsalted butter – ½ stick or 4 tablespoons or 2 oz.
  • ¾ cup brown sugar – 150 grams
  • 1-15 ½ oz can pineapple rings – about 6-8 drained – reserve the juice.
  • Maraschino Cherries – about 12 drained.

For the Yellow Cake:

  • 1 ½ cup all-purpose flour – 180 grams
  • 1 cup sugar – 200 grams
  • ½ cup unsalted butter – 1 stick or 4 oz at room temperature
  • ½ cup milk – 120 ml at room temperature
  • 2 eggs – room temperature
  • 2 tbsp pineapple juice – from the pineapple can
  • 1 ½ tsp baking powder
  • ½ tsp salt
  • ½ tsp vanilla extract
  • ¼ tsp almond extract


Pineapple base:

  • Preheat the oven to 375℉ and place the unsalted butter in a 9-inch round pan. Place the pan with the butter in the oven until it melts completely. Don’t forget about it! It should take just about 5-6 minutes or less if you cut the butter into smaller pieces.
  • Once melted, remove from the oven and sprinkle the brown sugar evenly around the base.
  • Arrange the pineapples starting with a whole ring in the middle. You could use whole rings around the entire base or cut rings in half and place them around the center pineapple ring.
  • Place a maraschino cherry in the center of each pineapple ring. If you’d like, you can also place them in the empty spaces between the rings (or half rings!).
  • Note the design here is up to you so do what feels and looks best to you too!

Yellow Cake:

  • In the bowl of a stand mixer or in a large bowl with a hand mixer, add all the cake ingredients together. Make sure your cold ingredients are now at room temperature.
  • With the mixer on low, beat until well combined, scraping the sides constantly to incorporate all the ingredients. Once combined, increase the speed and beat for 5 minutes for a hand mixer or about 2 minutes for a stand mixer. Constantly scraping the sides of the bowl.
  • Carefully pour the batter into the prepared cake pan on top of the pineapples, smoothing the top with a spatula and cutting through the batter to remove any large air bubbles. Be careful not to cut too deep or the design with the pineapples will move.
  • Bake for 30-35 minutes or until a toothpick inserted in the middle comes out clean or with just a few crumbs. The cake will be golden brown and should spring back slightly when pressed with your finger.
  • Cool in the pan over a wire rack for 10 minutes before unmolding.
  • To unmold, loosen the cake from the sides with a thin spatula. Using oven mitts, place a large plate on top of your cake mold and invert both. Now the plate should be at the bottom and the cake pan on top. Lift the pan straight up to discover a beautiful pineapple cake. The cake should release easily, however, if the fruit has stuck to the pan, lift it off with a spatula and replace it in the design of the cake.



  1. Make sure ALL cake ingredients are at room temperature before mixing them all together. Cool ingredients may result in pockets of fat trapped in the cake, leaving large holes.
  2. Let the cake rest for 10 minutes in the pan before inverting. Inverting too soon may make the cake fall apart. Waiting too long and the caramel may set and make the cake stick to the bottom of the pan.
  3. Flip the pan onto the plate confidently! Not doubting here is crucial for success.
Keyword Pineapple Cake, Pineapple dessert, Pineapple Upside Down Cake, Upside Down Cake

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