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

Pineapple Upside Down Cake FAQs

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 starting 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.

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 over-ripe to get the sweetest flavor.

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.

Pineapple Upside Down Rum Cake Recipe

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. 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 the brown sugar. Remember this will be the top of your cake, so you’ll want it to look nice.

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 comes clean from the center of the cake. 

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

Turn the cake upside down onto a heat safe plate. 

Serve this pineapple upside down rum cake warm and enjoy! 

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!