Pineapple Upside Down Cake

If you’ve never tried to make a pineapple upside down cake, you must try this semi-homemade recipe (with a brown sugar twist)! 

Pineapple Upside Down Cake

Want to Save This Recipe?

Enter your email & I'll send it to your inbox. Plus, get new recipes from me too!

Please enable JavaScript in your browser to complete this form.

By submitting this form, you consent to receive emails from Pizzazzerie.

One of my father’s favorite desserts is pineapple upside down cake, and I finally have the absolute best recipe to make for him the next time he visits from Texas. It’s absolutely a breeze to make, and tastes incredible.

Pineapple Upside Down Cake

Pineapple Upside Down Cake definitely fits the bill for an old-fashioned, “retro recipe”, but it’s one that still has a lot of popularity today. Note: Rum Cake is another retro recipe that’s making a comeback! It’s perfect for an end of summer bash, or an anytime treat since you can easily find pineapple rings year-round. The maraschino cherries are just so pretty on top of the rings too, so it’s definitely a dessert that looks wonderful on display.

This is a bit of an unusual recipe as the pineapple slices are placed on a buttery brown sugar combo so when it’s flipped back over, there are toffee-like pieces all over the cake. This is where the good stuff is, y’all!

Pineapple Upside Down Cake

I love fully homemade recipes, but every once in a while, a semi-homemade one does the trick! This recipe embellishes a pineapple cake mix to make it over the top amazing. You can also use a vanilla cake mix if the pineapple is too overwhelming. I love a lot of pineapple flavor though, so I use the pineapple cake mix.

Let’s get to the recipe, shall we? Now, I know one of the questions I will get is whether or not to use the cake mix dry or follow the instructions on the back of the box. Just use the mix. Ignore the instructions on the back. I’ve included the oil, eggs, etc in the recipe below. So when it calls for the cake mix, you just dump it on in dry. Easy!

The brown sugar and butter baked into the bottom of the cast iron skillet gives the top of the cake (when it’s flipped upside down) the most amazing flavor. You might see little sections of extra brown sugar – go for that slice, they taste so good! :)

Pineapple Upside Down Cake

Pineapple Upside Down Cake

Pineapple Upside Down Cake

A semi-homemade version of an old-fashioned pineapple upside down cake! 
Prep Time 10 minutes
Cook Time 30 minutes
Resting Time 5 minutes


  • 3 cups light brown sugar
  • 3/4 cups butter - (1.5 sticks)
  • 1 box pineapple (or vanilla) cake mix
  • 1 cup water
  • 3 large eggs - (room temperature)
  • 1/3 cup vegetable oil
  • 1 can pineapple slices
  • 7-10 maraschino cherries - (for garnish)


  • Preheat oven to 350 degrees F. 
  • Spray a standard (10”) cast iron skillet with non-stick cooking spray. Place on a medium-high stovetop. 
  • Add butter and brown sugar. Cook until fully melted and bubbling. 
  • Arrange the pineapple slices evenly over the top of the sugar (about 7 slices). 
  • Using an electric or hand mixer, combine cake mix, water, eggs, and oil. 
  • Pour cake batter over the pineapple slices. 
  • Transfer cast iron skillet to oven and bake for about 30 minutes. 
  • Remove from oven and allow to rest for 5 minutes. 
  • Carefully flip the cake onto a large plate or cake stand, and add a maraschino cherry to the center of each pineapple ring. 


Calories: 598kcalCarbohydrates: 109gProtein: 4gFat: 17gSaturated Fat: 10gCholesterol: 92mgSodium: 521mgPotassium: 151mgSugar: 88gVitamin A: 505IUVitamin C: 0.5mgCalcium: 183mgIron: 1.8mg
Tried this recipe?Let us know how it was!

I love the tart sweetness of the pineapple with all the brown sugar. It’s a dynamite flavor combination!

Can you store this pineapple upside down cake in the refrigerator?

Yes! I suggest no more than 3 days, if your cake even lasts that long! It’s so delicious!

I hope you’ll try out this pineapple upside down cake soon! Meanwhile, below are a few of my other favorite desserts!

Pizzazzerie is a participant in the Amazon Services LLC Associate Programs and other affiliate services. This means that receives a small commission by linking to and other sites at no cost to the readers.

Courtney’s Latest book

Get Your Copy!

In The Southern Entertainer’s Cookbook, Courtney Whitmore shares her party go-tos, over 75 delicious crowd-pleasing recipes. Featured as a must-have cookbook in Southern Living Magazine.


Leave a Reply

Your email address will not be published. Required fields are marked *

Recipe Rating