Easy Pineapple Upside Down Rum Cake with Boxed Mix

This rum soaked pineapple upside down cake is a sweet taste of the tropics! Keep scrolling to learn how to make pineapple upside down rum cake!

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As a professional hula dancer, I have danced at countless backyard luaus throughout the past 20 years.

Usually, the hosts invite me to eat dinner with them, and what’s ALWAYS for dessert? Yep, pineapple upside down cake. And I swear I’ve tried at least 50 different pineapple cake recipes.

I find that some of the best pineapple upside down cake recipes include a bit of rum. It gives such a nice flavor to the cake!

So, I’m sharing my recipe for pineapple upside down cake that reminds me of Hawaii. Yes, there’s rum in it!

Check out my Instant Pot Pina Colada Dump Cake recipe too!

Brief History of Pineapple Upside Down Cake

People have been making upside down cakes with fruit since the Middle Ages. That’s because they baked cakes in cast iron skillets, where it made sense to add the fruit first and then pour the batter on top.

Fast forward to the early 1900s in Hawaii, where pineapple plantations started taking off. They started canning pineapple rings at the Dole Plantation, and the idea of the Pineapple Upside Down Cake was born.

The first recorded pineapple upside down cake recipe was recorded in the 1930s, but the cake really became popular in the 1950s and 1960s.

What’s the Best Tropical Rum to Use?

Personally, I’m partial to Koloa Rum because it’s made on Kauai. It’s probably the best Hawaiian rum. Pineapple rum is quite delicious too.

However, you can totally use any Caribbean rum, too. I’d stick with regular rum versus flavored rum so that the pineapple flavor is balanced.

Canned Pineapple vs. Fresh Pineapple

You can use either for this recipe. While I usually recommend that people cook meat with canned pineapple instead of fresh pineapple (because of the bromelain enzyme), it doesn’t matter in terms of baking.

If you are going to use fresh pineapple, wait until your pineapple is overripe to get the sweetest flavor. If you don’t want to do all the work for a fresh pineapple, pineapple slices from the can work just as well for your rum and pineapple cake.

Pineapple Upside Down Cake Variations

If you really want to dress it up, add halved maraschino cherries to the center of the pineapple rings. Not only does this look pretty, but it tastes great!

You can also add shredded coconut for more of a pina colada flavor to the cake.

And you can always add nuts to change up the texture. Some love to eat this delicious dessert with whipped cream on top too or with a caramel topping.

Pineapple Upside Down Rum Cake Recipe

If you love pineapple upside down rum cake, you will absolutely love this recipe! Here is the best boozy pineapple upside down cake.

Ingredients for Pineapple Upside Down Cake with Rum:

• 1 cup rum 
• ¼ cup butter 
• 1 cup brown sugar, packed 
• 1 can pineapple rings, drained (reserve the juice)
• 1 can pineapple tidbits or crushed pineapple, drained 
• 1 box vanilla or pineapple cake mix 
• Vegetable oil & eggs per box mix instructions 

How to Make Pineapple Upside Down Rum Cake

Place the drained pineapple rings in a shallow dish and cover with rum. Arrange pineapple slices so all of them can soak in the rum. Let it soak overnight or at least for a couple of hours so it can soak up the flavor. 

Preheat your oven to 350 degrees or per your box cake mix instructions. 

Prepare your cake mix per package instructions, using the reserved pineapple juice instead of a portion of the water needed. 

Melt the butter in a 13×9 baking dish. Be sure to get it everywhere so your cake won’t stick when you flip it upside down.

Next, sprinkle brown sugar evenly over the melted butter. This is to help caramelize the pineapple and give it a nice browned look.

Evenly space the pineapple rings on top of the brown sugar. Remember, this will be the top of your cake, so you’ll want it to look nice. Arrange pineapple slices to look good!

Sprinkle on the pineapple tidbits to fill in any empty spots.

Now, pour the prepared cake batter on top of the pineapple rings and tidbits.

Bake per box mix directions or until a toothpick inserted comes clean from the center of the cake and it is golden brown.

After you take it out of the oven, immediately run a knife along the sides of the cake pan and let the cake cool for 5 minutes. 

Turn the upside down pineapple cake with rum upside down onto a heat-safe plate. 

Serve this pineapple upside down rum cake warm, and enjoy! 

Pineapple Upside Down Cake FAQs

Pineapple and Rum Upside Down Cake Wrap Up

This is my favorite dessert, especially for a Luau. If a classic pineapple upside down rum cake is your favorite cake, you will love this pineapple rum cake recipe too!

It is so easy to make this pineapple rum cake with cake mix instead of starting from scratch, so next time you want classic pineapple upside down cakes, try this pineapple rum version!

Looking for more Hawaii dessert recipes? Learn how to make Homemade Pineapple Ice Cream, Dole Whip, Pina Colada Dump Cake, or Easy Pineapple Coconut Cake!