Pineapple Upside Down Cake with Crushed Pineapple and Cake Mix

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Pineapple upside down cake with crushed pineapple and cake mix is absolutely delicious.

Pineapple upside down with crushed pineapple and cake mix is the best because it is easy to make and delicious to eat. My homemade version of this old fashioned classic starts by making a decadent brown sugar caramel in the bottom of a 9×13 pan, then laying down canned and fresh pineapple rings, along with maraschino cherries, on top of the brown sugar.

I then pour in a quick cake batter made with a box of white cake mix, crushed pineapple, sour cream, and a few special ingredients that really take this cake to the next level. After flipping the upside down cake out of the pan, I enjoyed one of the most delicious pieces of cakes yet. If you want to learn how to make an old fashioned pineapple upside down cake, keep reading!

Pineapple Upside Down Cake History

Homemade pineapple upside down cake has an interesting history. It is considered a “retro” recipe because it was popular in the 1950’s, 60’s, and 70’s.

In the United States, pineapple upside down cake was a very popular homemade cake in the 1950’s, 60’s, and 70’s: that’s why your grandma probably has a recipe for this cake, lol. However, the story of this cake goes back much farther:

According to, the term “upside down cake” first appeared in the late 1800’s and was used to describe cakes that people made on top of the stove in cast iron skillets. At that time, not everyone had ovens like they do today, so making cakes on the stove was more common.

People used all kinds of fruit like apples and peaches, but it wasn’t until 1901 that using pineapple became common because that’s when Jim Dole’s Hawaiian Pineapple Company, today known as Dole plc, began producing canned pineapple on a large scale.

Dole Pineapple Cake Competition

The cake became even more popular after 1925 when Dole sponsored a contest for pineapple cake recipes. Surprisingly, 2,500 out of the 60,000 recipes submitted were for pineapple upside down cake.

Although the cake gained popularity in the 1920’s, it was still considered a rather elegant cake. In fact, according to a article, it wasn’t until the 1930’s that pineapple upside down cake came to be seen as a “homey” dessert like it was from the 1950’s onwards.

Can You Make Pineapple Upside Down Cake with Crushed Pineapple and Cake Mix in a Glass Pan (9×13)?

If you are wondering if you can make pineapple upside down cake in a glass pan, the answer is yes! Glass is perfect for baking because it distributes heat very well; in fact, all of my pie pans that I currently have are glass, and I think my pies bake up perfectly fine in them.

Actually, making pineapple upside down cake in a 9×13 glass pan is actually best, in my opinion:

  • Making sure that you fill the 2 pans equally isn’t an issue – That’s why I always use a food scale, lol.
  • You don’t have to worry about taking the cake layers out of the pan – That’s always nerve-wracking.
  • You’ll be able to see the bottom of the cake – Once you flip it over, so you’ll know if and where any pieces of pineapple or brown sugar stick to the pan.
  • The cake’s contact area is larger with the glass pan – So, you to add more brown sugar caramel and pineapple slices.

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Best of all, you don’t have to adjust the recipe is you’re using a standard box of cake mix in the United States: 1 15.25 oz box of cake mix is enough for either 2 8-inch pans or a 1 9×13 pan.

The biggest issue with making pineapple upside down cake in a glass pan is flipping the pan over: flipping a 9×13 pan is a big awkward, but it can definitely be done–keep reading to learn how I did it!

Fresh or Canned Pineapple for Upside Down Cake?

Most old fashioned recipes for homemade pineapple upside down cake call for putting rings of canned pineapple on “top” of the cake. Although canned pineapple rings are quick, easy, and uniformly sliced, there is no comparison in taste with fresh or frozen pineapple. In some ways, canned and fresh pineapple taste almost like different fruits, imo, the fresh is so much more flavorful.

If you have time, I HIGHLY recommend cutting up a fresh pineapple for the rings on the top of the cake. If you don’t want to cut up a whole pineapple, you can do what I did: use canned pineapple for the main design, and then fill in the other areas with pieces of fresh pineapple.

That way, you experience the taste of fresh pineapple in upside down cake, as well as make sure that there is pineapple in every bite–unlike the traditional recipe.

My pineapple upside down cake with crushed pineapple and cake mix recipe is the best version you will ever try because it’s both delicious and beautiful.

Pineapple Upside Down Cake with Crushed Pineapple and Cake Mix

Although my pineapple upside down cake with crushed pineapple and cake mix recipe is easy, there are a few steps that have to be done in a certain order. If you follow my recipe, you will see that’s the best homemade pineapple upside down cake you’ve ever tried.

Preparing the Brown Sugar Caramel

The first step in my pineapple upside down cake recipe is making the brown sugar caramel. I melted a stick of butter in the microwave and poured it into my buttered 9×13 glass pan. I then sprinkled in the light brown sugar, mixing the butter and sugar with my hands as I spread them out on the bottom of the pan.

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Originally, I only used 1 cup of brown sugar–that’s what other recipes online used. However, after mixing in 1 cup, it just didn’t look right to me, so I added a bit more, then even more, until I had added a total of 2 cups.

At one point I thought that 2 cups might have been too much sugar, but when I tried the cake, I knew that 2 cups was just right. I was VERY glad that I listened to my instincts and added more than 1 cup.

Making the brown sugar caramel for the upside down cake was a good example of how sometimes you have to trust your instincts and modify a recipe if it just doesn’t look right as you’re making it.

Laying Down the Pineapple Slices

After making the butter and brown sugar layer, it was time to lay down the pineapple slices. Although my original plan was to only used canned pineapple, I realized that I did not have enough canned pineapple to cover the cake. I remember a fresh pineapple I had on hand, so I decided to use both.

Since the canned pineapple rings were uniformly cut and had a good-sized hole for the maraschino cherries, I decided to use the canned pineapple to make 3 symmetrical rows in the middle of the cake.

Use Both Fresh and Canned Pineapple?

Cutting fresh pineapple into uniform slices is hard, so I decided to just the irregular slices into chunks. I then put the chunks around the rings of canned pineapple, covering the entire surface of the cake as best I could.

I then added maraschino cherries to not only the center of the canned pineapple rings but also randomly elsewhere in the cake to cover any holes and add color. By using both pineapple rings and pineapple chunks, I made sure that there would be pineapple in every bite.

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Mixing the Cake Batter

Once the brown sugar caramel and pineapple ring layers were in the glass pan, it was time to move on to making the cake batter. Since I used a standard box of white cake mix, the batter was super easy. I added:


  • Crushed Pineapple
  • Orange Jell-O
  • Sour Cream
  • Coconut Extract
  • Eggs
  • Canola Oil

*Shredded Coconut (more info in the next section)

Most old fashioned pineapple upside down cake recipes call for using the juice from the can of pineapple rings in the cake batter, but I wanted the cake to have even more pineapple flavor, so I added 1 cup of crushed pineapple.

Although I didn’t this in any other recipes, I also added 1 small box of orange Jell-O, along with 1 teaspoon of coconut extract. These ingredients might seem odd in a pineapple upside down cake recipe, but I add all 3 ingredients to my carrot cake recipe and hummingbird cake recipe, and they both turn out delicious.

In addition to the flavor, the orange Jell-O added a tinge of orange color to the cake that made it look more enticing. Most pineapple upside down cakes I saw online were white, so I thought adding more color would be a nice twist.

Add Coconut?

I don’t think I saw any recipes online that called for adding coconut, so I figured that including some in my recipe would be a bit controversial. That’s why I was originally going to leave it out, but when I remembered that I had 2 tablespoons of coconut in a little bag off to the side, I decided to use it up.

I had already mixed up the batter, so I sprinkled the coconut on top of the pineapple and maraschino cherries. I wanted the cake to be a pineapple upside down cake, so just 2 tablespoons was enough to give a nice hint of shredded coconut without competing with the star of the show.

Pouring In The Cake Batter

After mixing the batter and sprinkled in the shredded coconut, I poured the batter over the brown sugar and pineapple slices in the pan. My cake was then ready for the oven.

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How to Flip a Pineapple Upside Down Cake

Even though pineapple upside down cake is pretty easy, figuring out how to flip it right-side up isn’t as clear. Here’s how to flip a pineapple upside down cake so that it comes out perfectly:

  • Don’t wait too long – I waited 5 minutes before flipping my cake out of the pan. If you wait too long, the caramel will cool down and solidify, making it impossible for the cake to come out cleanly. So, let it cool down a few minutes so that you don’t burn yourself, but not much longer than 15 minutes tops.
  • Use 2 pot holders or towels – This job requires both hands, so make sure you have protection for both of them.
  • If using a 9×13 glass pan, flip the cake out onto a baking sheet – That’s probably the largest flat surface in your kitchen.
  • Make sure that the baking sheet’s flat interior is larger than the cake – Before flipping the cake, lay the baking sheet on top of the glass pan upside down. If the raises edges of the baking sheet are at the edges or beyond the edges of the 9×13 pan, you should be fine.
  • Line the baking sheet with foil – That will make cleanup easier.

Then, when you are reading to flip the upside down cake out of the pan:

  1. Put the baking sheet foil side down on top of the cake.
  2. Use your hand to hold both the cake pan and the baking sheet at the same time. Do this on both sides of the cake.
  3. In one, swift motion, flip everything so that what was the bottom is now the top. The bottom of the glass pan should now be on “top.”
  4. Gently shake the glass pan and baking sheet to loosen small bits of sugar or pineapple stuck to the pan.
  5. In order to lift the glass pan up and off of the cake:
    • Slide a thick knife between the glass pan and the baking sheet.
    • Use the knife as a lever to “lift” the glass pan up.
    • Still using pot holders or towels, slide your hand in the opening between the glass pan and the baking sheet.
    • Use that hand to pick up the glass pan and carefully remove it.
    • If there are any pieces of pineapple or bits of brown sugar stuck to the glass pan, scrape them off.

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Can You Make Pineapple Upside Down Cake the Day Before?

Although you probably can make pineapple upside down cake the day before, I recommend making it the same day you eat it. In fact, I recommend planning your meal so that you can serve the cake 30-60 minutes after taking it out of the oven.

One of the best parts of this cake is the brown sugar caramel, and I think its “ooey gooey” texture is more apparent when the cake is warm. I guess you would reheat the cake, but I still think that serving upside down cake soon after taking it out of the oven is best.

Variations of Pineapple Upside Down Cake with Crushed Pineapple

My recipe for pineapple upside down cake with crushed pineapple and cake mix is delicious, but there are a few variations I’d like to try in the future:

  • Bundt pan – You can’t get any more old fashioned than a bundt pan.
  • Cast iron skillet – Many southern pineapple upside down cake recipes use a cast iron skillet.
  • Crushed pineapple in the caramel – Instead of adding pineapple rings to the caramel, some recipes use crushed pineapple that is well drained. Using crushed pineapple would ensure that literally ever bite has some pineapple, so it’s worth exploring.
  • Pecans – I love pecans, and I think a bit of crunch in this cake would be good. But just add a few–like the coconut–you don’t want anything to compete with the pineapple in this recipe.
This is the best pineapple upside down cake recipe ever!

Recipe Review

Appearance: 10 / 10

This cake looks incredible. The brown sugar caramel, the pineapple, and the maraschino cherries on “top” of the cake looked amazing, especially since I used the canned pineapple rings to make a symmetrical pattern. The orange Jello-O added nice color to the cake layer, too.

Taste: 10 / 10

In terms of taste, this was the best pineapple upside down cake I have ever had. The combination of crushed pineapple and orange Jell-O in the cake was delicious, and the hint of coconut was a nice finishing touch.

The layer of brown sugar caramel was thick and butter, and the pineapple on top was plentiful. The fresh pineapple had a lot more flavor than the canned, so I highly recommend using fresh for the top.

Texture: 10 / 10

The texture was very nice. The cake was light and fluffy, and the brown sugar caramel was soft and gooey–in a good way. Some of the caramel seeped down into the cake, making it very moist.

Ease: 9.5 / 10

This pineapple upside down cake was super easy to make, especially since I used cake mix to make the batter. However, considering the number of steps involved, and the fact that you may have to cut up a fresh pineapple for maximum flavor–I will downgrade this recipe very slightly.

Possible Changes to the Recipe

This recipe was a big success, so if I make it again, I probably won’t change anything–except maybe use all fresh pineapple on “top.” Other than that, I wouldn’t change a thing.

Pineapple Upside Down Cake with Cake Mix and Crushed Pineapple Recipe

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About the Author: Thien Bao

Hello, my name is ThienBao. I am a freelance developer specializing in various types of code.