Cast Iron Pineapple Upside Down Cake

Hey Y’all!  I did not know how much people LOVE pineapple upside down cake until I posted a poll in my Instagram stories. Like y’all love y’all some pineapple upside down cake.  Until now, I would skip a slice of pineapple upside down cake if it were the only dessert available.  But so many people in my comments let me know that I’ve been doing it wrong.  You’re supposed to eat this cake WARM.  Mind Blown.  So of course I had to get on my zoom and make a pineapple upside down cake in a cast iron skillet.   This recipe features the classic caramelized pineapples and cherries, with a bit of ginger for kick.  And to make things easier, this recipe starts off with a yellow cake mix! Here’s how you can make this classic dessert at home.

The story of the pineapple upside-down cake begins in the early 1900s when canned pineapple became widely available due to advancements in canning technology. James Dole, the founder of the Hawaiian Pineapple Company, later known as Dole Food Company, played a significant role in popularizing pineapple in American kitchens. In 1925, the Hawaiian Pineapple Company sponsored a recipe contest, which received thousands of entries featuring pineapple. Among them, the pineapple upside-down cake stood out, capturing the hearts and taste buds of many.

The cake became especially popular in the South, where homemakers appreciated its simple preparation and stunning presentation. The combination of buttery cake, caramelized fruit, and the maraschino cherry's vibrant red hue quickly earned it a spot on the dessert tables of Southern homes.  In the south pineapple upside down cakes were quickly made using cast iron skillets, because a well-seasoned cast iron skillet is essentially a non-stick pan.  

Jump to:

• Ingredients
• Kitchen Equipment
• Mise En Place
• How to Make Cast Iron Pineapple Upside Down Cake
• Pineapple/Cherry Design Ideas
• Tips for Success
• Serving, Reheating & Storing Notes
• Variations/ Substitutions
• Related
• Recipe
• Recipe

Ingredients

• 1 box (15.25 ounces) yellow cake mix*
• Pineapple juice
• Water
• Vegetable oil
• Large eggs
• Vanilla extract
• Ground ginger
• Unsalted butter
• Brown sugar
• Pineapple slices
• Maraschino cherries
• Ground ginger
• Kosher salt

*Shrinkflation is real y’all.  If your cake mix is less than 15.25 ounces, follow the package instructions for water, oil and eggs.   It’s important to note the pineapple juice replaces most of the water.  For example:  in my recipe the can of pineapples had ¾ cup of juice and the instructions called for 1 cup of water = ¾ cup pineapple juice + ¼ cup water. 

Kitchen Equipment

• 9 or 10 inch cast iron skillet
• Measuring cups/spoons
• Large and small mixing bowls
• Flexible Spatula
• Whisk
• Hand Mixer
• Pot holders
• Wire rack 
• Cake plate/large cutting board 

Mise En Place

When using a hot cast iron skillet, I am always worried that I will forget that the skillet is hot and will burn myself.  In order to prevent that, I spend a lot of time prepping all of the components so that when I am ready to mess with the hot cast iron skillet, I can focus solely on not burning myself.  What does this mean for this recipe?  It means laying out the pattern for the pineapple rings and cherries, mixing the cake batter and mixing the topping ingredients while the cast iron skillet is heating in the oven. 

How to Make Cast Iron Pineapple Upside Down Cake

1: Preheat and Prepare

1. Place a cold cast iron skillet into the oven and set the oven temperature to 400ºF.
2. Drain the pineapple juice into a measuring cup and set it aside.
3. On a paper plate or sheet of parchment paper, lay out the pineapple rings in your desired pattern.
4. Put the drained cherries in a bowl.
5. In a small bowl, whisk together the brown sugar, ground ginger, and kosher salt for the topping. Set aside.

2: Make the Cake Batter

1. In a large bowl, combine the cake mix, pineapple juice, water, vegetable oil, eggs, vanilla extract, and ground ginger.
2. Blend the mixture with a hand mixer on medium speed for about 2 minutes until smooth.

3: Assemble the Pineapple Upside Down Cake

1. Remove the heated cast iron skillet from the oven and set it on a heat-proof surface. Reduce the oven temperature to 375ºF.
2. Melt the stick of butter in the skillet. Then, stir in the brown sugar mixture, ensuring it creates an even layer across the bottom of the pan.
3. Carefully place the pineapple rings and cherries in the pan according to your chosen pattern.
4. Pour the prepared cake batter over the pineapples and cherries.

4: Bake the Cake

1. Bake the cake at 375ºF for 10 minutes.
2. Reduce the oven temperature to 350ºF and continue baking for an additional 35 to 40 minutes. The cake is done when a toothpick inserted into the center comes out clean.

5: Serve Your Masterpiece

1. Remove the cake from the oven and immediately flip it onto a serving plate or cutting board. Since the cast iron skillet is so heavy and also very hot, choose a plate that is more lightweight.  Your arms will thank you. 
2. Serve the cake immediately while it's warm and enjoy the delightful combination of caramelized fruit and moist cake.

Pineapple/Cherry Design Ideas

There are so many ways that you can create a pattern with the pineapples and cherries! I taped a piece of parchment paper to my countertop and traced the size of my skillet onto the paper.  From there I played around with designs until I found one I liked the best. 

Tips for Success

• Use the Canned Pineapple Juice: Freshly drained pineapple juice enhances the flavor of the cake. The recipe calls for ¾ cups
• Even Caramelization: Ensure the brown sugar mixture is evenly spread at the bottom of the skillet to achieve uniform caramelization.
• Immediate Flipping: Flip the cake onto the serving dish immediately after removing it from the oven to prevent the topping from sticking to the skillet.

Serving, Reheating & Storing Notes

Ideally the pineapple upside down cake is served warm.  Once the leftover has cooled, cover it with aluminum foil/ plastic wrap and refrigerate.  I repeat, pineapple upside down cake should be refrigerated. 

To reheat, I would set my toaster oven to 350ºF (on the Bake Function) and line a quarter sheet baking pan with parchment paper.  The bake time will vary depending on the size of the slice – anywhere from 5 -10 minutes. 

Variations/ Substitutions

• Crushed Pineapple instead of pineapple rings.  I recommend crushed pineapples if you want to make sure that every single bite has a bit of caramelized pineapple. 
• Fresh pineapple rings instead of canned.  Fresh pineapples will only make this recipe better! Bonus points if you can get the pineapple in season and on sale. 
• The ground ginger is optional.  I love the combination of ginger and pineapple– but it’s definitely a personal preference. 

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