Pineapple Upside Down Cake

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The old-fashioned Pineapple Upside Down Cake is a simple and classic dessert that everyone loves. This recipe is an easy one courtesy of a vanilla cake mix that is jazzed up with a homemade caramel, canned pineapple rings and maraschino cherries. This cake has never been so good! Check out my other classic cake recipes here.

Pineapple Upside Down Cake Basics

If you have never made one of these cakes before, it’s made up of two basic parts:

1. The Pineapple Topping which is made with butter and brown sugar melted together, then topped with drained pineapple rings and maraschino cherries.
2. The Cake Batter which is just a cake mix made as directed with water, oil and eggs.

Yes, I Use a Cake Mix

While I tested this recipe with a homemade vanilla cake, I much preferred it made with the cake mix. Not only was it faster process start to finish, I found the finished overall cake had a better texture. Plus those darn cake mixes tend to turn out every time! It’s a nice reliable ingredient.

Either a white, yellow or vanilla cake mix works perfectly for this recipe. I used a Betty Crocker 15.25 oz box of vanilla cake mix.

The unsung hero of this recipe are the cherries. Here are other cherry recipes you should try: Tart Cherry Pie-can make this with frozen or canned cherries | Cherry Almond Cookies-really old recipe off my site, but so so good! | Cherry Almond Chex Mix-great for packaging up as gifts for the holidays.

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Three Tips Before You Begin

So, the intimidating part about Pineapple Upside Down Cakes is flipping it upside down to serve it. The caramel, pineapple rings and cherries that you put in the bottom end up being the top of the cake and a pretty sticky concoction after baking. Here are three tips to give you the confidence to forge ahead:

1. Use a glass 9×13 baking dish. This allows you to see exactly what is happening as the cake bakes, but also what is happening when it comes time to flip up out. Glass also doesn’t give you extra brown edges like a metal or darker teflon would. That’s not to say you *can’t* use a metal pan because you can, you just need to watch it a little more closely and bake it in the center of the oven to minimize crispy edges.
2. Use plenty of nonstick cooking spray. Now is not the time to use butter and flour. In my experience,  it’s not enough of a coating to keep those pineapple rings from sticking. Use the spray and be generous.
3. Wait 10 minutes after baking before turning the cake out. This gives the cake enough time to settle and become a little more sturdy, plus the caramel sauce needs to tighten up a little bit so it doesn’t go running all over the serving dish.

I will say the beautiful thing about this cake is if some of the pineapple or cherries happen to stick to the cake pan, just pull them out of the pan carefully and replace back onto the cake. 

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How to Make Pineapple Upside Down Cake

I promise this isn’t a super hard cake to make. It comes together in about 15 minutes and is perfect at room temperature for a few days as long as its covered with plastic wrap. Here’s how to make it:

Make the Pineapple-Caramel Topping

Melt butter and brown sugar together in a medium skillet until melted. Bubble for 1 minute, then pour into well greased 9×13 glass baking dish.

Drain the pineapple rings well and blot each one with paper towel. Do the same with the maraschino cherries. Place the pineapple rings into the bottom of the pan, overtop of the caramel. Fill in any extra spaces with the cherries. Set aside.

Make the Cake

Empty out cake mix into a large bowl. Make cake according to package directions stirring together with water, vegetable oil and eggs. Pour batter overtop pineapple and smooth the top. Bake entire cake at 350 degrees for 40 minutes or until golden brown and toothpick comes out clean after being inserted.

Flip the Cake Out to Serve

After the cake has cooled 10 minutes, loosen edges with a butter knife. Add a serving plate to the top of the cake pan, then flip upside down to remove cake from pan. If some of the pineapple or cherries happen to stick to the cake pan, just pull them out of the pan carefully and replace back onto the cake. 

Enjoy warm or at room temperature. 

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Cake Storage Directions

Any pineapple upside down cake (and any cake for that matter) can keep around three days at room temperature as long as it is covered with plastic wrap. As the days go on, you will be able to tell that it’s getting a bit older, but a quick 10 second zap in the microwave should do the trick. I don’t recommend refrigeration for this cake because I don’t want the butter and brown sugar to recrystallize or harden in any way.

Love Cake? Here are some Old Fashioned Favorites:

• Italian Cream Cake– a show stopping cake everyone loves! A classic cake that has been around for years.
• Red Velvet Cake– bright red, soft and moist cake with cream cheese frosting. SO good!
• Apple Cake– truly an old school, super simple recipe made in a round cake pan and topped with powdered sugar
• Coconut Cake– if you love coconut, give this amazing recipe a try! So light and coconutty!
• Cinnamon Streusel Coffee Cake– another cake mix based recipe that is a classic! A great weekday recipe.

More Tropical Treats to Try!

• Pina Colada Cookies with Rum Glaze
• Non Alcoholic Pina Coladas (Virgin)
• Fruit Pizza or Fruit Pizza Cookies
• Coconut Lime Pudding Cups
• Banana Coconut Cream Pies

Anyways, I hope you love this recipe as much as me and my family did! It’s really a traditional but approachable recipe that everyone loves. And don’t forget that cooking spray! Have a great day, friends.