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Pineapple Upside Down Cake from a Box Mix

It’s so easy to turn a yellow cake mix into this easy Pineapple Upside Down Cake! One can of sliced pineapple rings, 1 cup of brown sugar, some maraschino cherries, and the usual ingredients for a boxed cake mix. . .and you’re good to go. Talk about an easy dessert!

This is one of those classic recipes that most home cooks have in their arsenal. If you haven’t make this delicious cake before, it’s time to try it now!

I don’t know why I had Pineapple Upside Down Cake on the brain, y’all. I think maybe I saw a picture of one? They’re so pretty, all of those colors blended together–the bright red cherries, the yellow rings of pineapple, and the luscious cake. I just knew that I had to bake one!

The History of Pineapple Upside Down Cake

pineapple upside down cake from out of the box baking.com

As I pondered the recipe for this cake, I got to thinking about the idea of flipping a cake upside-down with fruit making its way to the top. Who came up with this idea, anyway? According to food historian Gil Marks, the original idea came from a variety of historic baked goods, including skillet cakes. Not everyone had an oven 100 years ago. So, baked goods like cornbread, shortcakes, and so on were baked in a skillet and then flipped.

It became trendy to put fruit on the bottom of the cake before baking. The French tarte tatin, for instance, was an apple tart flipped upside down. It dates back to the early 20th century.

There were a host of other upside-down treats available back then, as well, but the Pineapple Upside Down Cake is still causing party-goers to flip (in a good way).

A Yummy Pineapple Upside Down Cake Recipe

I hadn’t baked a pineapple upside down cake in years and needed a refresher, so off to the web I went. I searched for a recipe that started with a boxed mix. (Hey, if you’ve been following me for a while you know that I most often start my cakes this way.)

I found a recipe on the Betty Crocker site. Don’t tell Betty, but I used a Pillsbury mix.

This moist, tasty cake is so easy to whip up. Best of all, the colors are impressive! I think they’re reminiscent of a stained glass window. Talk about a dessert that’s easy on the eye!

Pineapple Upside Down Cake Ingredients

So, what will you need to make this easy dessert? You’ll find a full printable recipe at the bottom of this post but for now, here’s a quick glance at the items you’ll need to gather.

pineapple upside down cake from out of the box baking.com
  • yellow cake mix
  • large eggs
  • oil
  • butter
  • light brown sugar
  • canned pineapple slices (rings)
  • pineapple juice (reserved from can of pineapple rings)
  • maraschino cherries (without stems)

Whipping up this cake is as easy as 1-2-3!

1: Melt your butter in the bottom of a 9×13 pan and sprinkle the brown sugar across the melted butter. (If you start with room temperature butter, the melting process is easy!) I love the tartness of salted butter but you might prefer unsalted butter. If you prefer to use a round cake pan, use a 10-inch cake pan.

2. Place your pineapple rings and maraschino cherries on top of the brown sugar. (You can add more cherries between pineapple rings if you like!)

3. Make your yellow cake mix according to directions, replacing the water with the reserved pineapple juice. (Basically, combine your eggs, oil, and pineapple juice and mix until incorporated.) I used a stand mixer with the paddle attachment but you could certainly mix by hand in a medium bowl or use a hand mixer.

Once you’ve got it mixed, pour the cake batter over the fruit and bake in a preheated 350 degree oven for 42-45 minutes or until the cake springs back to the touch.

Run a knife around around the sides of the pan then cool for a few minutes on a wire rack. Flip the cake onto a heat-proof dish or tray and leave the baking pan on top for five minutes so any excess liquid can drain down. Remove the pan and allow the cake to cool for 15 minutes before slicing and serving. (I was surprised to see that nothing stuck to the bottom of the dish!)

The top of this cake is ooey, gooey, caramelly, and delicious! (Is there anything better than sticky caramelized pineapple?) The sweet pineapple flavor will leave you hankering for the tropics!

Some people prefer their Pineapple Upside Down Cake warm; others like it cold from the refrigerator. No matter how you slice it up, it’s yummy! And talk about a moist cake!

You can place in an airtight container and store in the refrigerator. If you choose to cover with plastic wrap, make sure it’s not stuck to the fruit or you’ll make a mess pulling it off.

Variations on Pineapple Upside Down Cake

This is a classic pineapple upside down cake but the next time I make this recipe I’ll probably vary things a bit. Maybe I’ll throw in some pecans or walnuts. Maybe I’ll use crushed pineapple instead of rings. I love to mix things up. Maybe you do too! Here are some suggestions:

  • Make this cake in a cast iron skillet. Fun!
  • Make a pineapple upside down bundt cake!
  • Don’t have canned pineapple? You can use fresh pineapple. Cut it into thin wedges or fresh pineapple rings.
  • No canned or fresh pineapple? Do you have pineapple topping? That will work in a pinch.
  • Want more of a cherry flavor? Add some of the maraschino cherry liquid to the batter!
  • Add a bit of vanilla extract or vanilla bean to your batter for a more enhanced flavor.
  • For a full Hawaiian flavor, add coconut to the pineapple and cherry mixture.
  • I plan to make a Pineapple Upside-Down Dump Cake soon! When I do, I’ll link back to this post.
  • Skip the pineapple and use mango or other fruit of your choice. Apples are a good option, as well. You might even used canned peaches (adding the juice to the cake mix). Just pour batter on top of your fruit.
  • Speaking of pouring the batter. . .use a different flavor cake! Try lemon or French vanilla!
  • Only have a white cake mix? No problem! Use butter in place of oil to turn your cake that lovely yellow color.
  • Make your cake richer by adding sour cream in place of some of the liquid.
  • Use extra egg yolks for a richer cake. This will also enhance the yellow color of the cake if you’re using a white cake mix.
  • Wanting to go a completely different route? Why not try a Chocolate-cherry upside-down cake?

Questions People are Asking about Pineapple Upside-Down Cake

Can I make a skinny version of Pineapple Upside Down Cake?

Sure! You can use a sugar-free yellow cake mix and unsweetened pineapple. Use a brown sugar substitute in place of traditional brown sugar.

Can I make this into a Pina Colada Pineapple Upside-Down Cake?

Yep! Just add one cup of shredded coconut to the recipe and substitute coconut milk for the pineapple juice!

Can I make a layered pineapple upside-down cake?

Sort of. You can make a yellow cake mix according to the box’s directions but add a full can of crushed pineapple in place of water. Add some diced maraschino cherries, if you like. Bake in two 8″ round pans and layer with buttercream frosting and rings of pineapple between them, along with more maraschino cherries.

Can I make Pineapple Upside-Down Cake in mason jars for individual servings?

Yes! Check out this amazing recipe from Totally the Bomb.

How do I store Pineapple Upside-Down Cake?

Stick toothpicks on top and cover with plastic wrap. If you’re planning to wait more than 24 hours to serve, refrigerate and then bring to room temperature before serving.


Making Pineapple Upside Down Cake

Feeling Fruity, but Not in the Mood for Pineapple?

No problem! I’ve got lots of other fruit-based cakes to choose from.

Interested in more tasty recipes? Check out this week’s offerings over at Miz Helen’s Full Plate Thursday! 

Pineapple Upside Down Cake from a Box Mix

Pineapple Upside Down Cake from a Box Mix

Yield: 12
Prep Time: 10 minutes
Cook Time: 45 minutes
Additional Time: 15 minutes
Total Time: 1 hour 10 minutes

This luscious pineapple upside down cake is easy to make with a boxed yellow cake mix.

Ingredients

  • 1 box yellow cake mix
  • 3 large eggs
  • 1/2 cup vegetable oil
  • 1/4 cup butter (salted or unsalted)
  • 1 cup brown sugar
  • 1 can pineapple rings
  • pineapple juice (reserved from can of pineapple rings)
  • maraschino cherries (without stems)

Instructions

    Whipping up this cake is as easy as 1-2-3!

    1: Melt your butter in the bottom of a 9x13 pan and sprinkle the brown sugar across it.

    2. Place your pineapple rings and maraschino cherries on top of the brown sugar. (You can add more cherries between pineapple rings if you like!)

    3. Make your yellow cake mix according to directions, replacing the water with the reserved pineapple juice. (Basically, combine your eggs, oil, and pineapple juice and mix until incorporated.)

    Once you've got the cake mixed, pour it over the fruit and bake in a preheated 350 degree oven for 42-45 minutes or until the cake springs back to the touch.

    Flip the cake onto a heat-proof dish or tray and leave the baking pan on top for five minutes so any excess liquid can drain down. Remove the pan and allow the cake to cool for 15 minutes before slicing and serving.

    Notes

    Some people prefer their Pineapple Upside Down Cake warm; others like it cold from the refrigerator. No matter how you slice it up, it's yummy!

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    Barb Witt

    Wednesday 6th of April 2022

    This is Todd's favorite! I'm not crazy about the boxed pineapple upside down cake, and this one sounds delicious! I'm making this for Easter!

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