Skillet Pineapple Upside Down Cake

This lovely Skillet Pineapple Upside Down Cake is such a delightful treat! The cake is moist, buttery and crumbly, with a caramelized brown sugar topping layered with pineapple rings and maraschino cherries.

I love making my pineapple upside down cake in a cast iron skillet. It is easy, quick, and produces the best brown sugar crust.

Some of my other favorite cake recipes on the blog includes Italian Ricotta Cheesecake, Molten Chocolate Lava Cake, and Strawberry Shortcake Angel Food Cake. Don’t forget to check them out! They are pretty fabulous if I must say!

Pineapple Upside Down Cake in Cast Iron Skillet

I have loved pineapple upside down cake for as long as I can remember. I adore its caramelized brown sugar crust, and that moist and dense cake loaded with sweet tropical flavors of pineapples.

One of my favorite ways to make pineapple upside down cake is using a cast iron skillet.

Skillet pineapple upside down cake is first baked with the caramelized brown sugar crust and pineapple rings at the bottom, while cake batter is baked sitting on top of the crust and toppings.

After baking, cake is flipped upside down and served with the caramelized brown sugar pineapple crust on top.

The cake in our skillet pineapple upside down cake is moist, crumbly, slightly dense and loaded with fruity flavors of brown sugar and pineapple. It’s seriously delightful.

Cast iron skillets are some of the most handy and hardy cookware you’ll come across in the kitchen. If you don’t have a basic cast iron skillet, I highly recommend getting one, and most likely it will last you your entire life. You really have to work very hard to destroy it.

In addition, cast iron skillet is also super reasonably price and can be used both on the stovetop and in the oven, which makes it so convenient.

Here are all the reasons why I love making this skillet pineapple upside down cake:

• I have the option to melt the butter and subsequently create a nice caramelized brown sugar texture by cooking it on the stovetop before baking the cake in the oven.
• Cast iron has a natural non-stick finish and it is easy to detach cake from skillet after baking
• Cast iron heats evenly and has great heat retention
• Cast iron is tough and hard to scratch up or break

Ingredients

Here are all the ingredients you will need to make skillet pineapple upside down cake. Let’s talk about it in two categories, the topping and the cake:

Toppings:

• pineapple rings – traditionally, canned pineapples are used and I honestly prefer it to fresh for this. It is easier to just get pre-cut rings that comes in a can than try to cut up a fresh pineapple in rings. Also, the canned pineapples are often softer and slightly sweetened, which makes it a better fit in the cake. I know I typical go for the fresh item vs. canned, but this is a special scenario!
• maraschino cherries – this is a preserved, sweetened cherries that typically comes in a bottle, soaked in syrup.
• brown sugar – brings yummy caramelized flavors to the topping. Do NOT substitute with granulated sugar.
• unsalted butter – try to use unsalted and not salted butter to control the salt level

Cake:

• all-purpose flour
• baking powder – rising agent for the cake
• baking soda – rising agent for the cake
• unsalted butter – softened or melted. Leave butter out for a few hours before baking, or defrost it in the microwave.
• brown sugar
• sour cream – yogurt can be used as a substitute
• milk – whole milk works best but any type of milk (except fat free) can be used as well. Cake is less soft and creamy when using lower fat milk.
• eggs
• vanilla extract – pure vanilla extract has the best flavor and taste.
• pineapple juice – I get this from the canned pineapple rings
• salt – helps balance the sweetness and bring out the flavors

How to make Cast Iron Skillet Pineapple Upside Down Cake

Step 1: Make the cake batter

When making skillet pineapple upside down cake, I always make the cake batter first, and I typically make the cake batter in just one bowl. This makes the process quicker, and there’ll be less dishes to wash. WINNER!!

Add all the wet ingredients first into a large mixing bowl or the bowl of stand mixer: softened butter, brown sugar, sour cream, milk, egg, vanilla extract, and pineapple juice from canned pineapples.

Mix everything up together, and then add the dry mixture: flour, baking powder, baking soda, and salt. Bring everything together and combine.

Step 2: Make the topping

To make the pineapple upside down cake topping, melt butter in a 12″ cast iron skillet.

Once butter has melted, switch off heat.

Sprinkle brown sugar all over butter, then top with pineapple rings (make sure to pat dry!) and maraschino cherries (remove stems).

Here’s how they are laid out on a 12-inch cast iron skillet.

This brown sugar-butter-pineapple-cherry combo will eventually be flipped upside down and form the topping or crust for our skillet pineapple upside down cake.

Step 3: Assemble cake

Pour cake batter onto the brown sugar-butter-pineapple-cherry concoction. Use a spatula to evenly spread out the batter so that it completely covers the pineapple rings, butter and brown sugar.

Step 4: Bake

Bake skillet pineapple upside down cake in the oven at 350℉ for 40 minutes.

Step 5: Flip it up side down!

When cake is done, remove from the oven and let it cool for about 20-25 minutes.

Then place a plate on the skillet, and flip the skillet upside down to remove cake.

With the amount of butter used and the non-stick quality of a cast iron skillet, I’ve never had a problem flipping a pineapple upside down cake within the hour of baking.

And here’s our lovely pineapple upside down cake…baked in a cast iron skillet!

The brown sugar caramelized top is loaded with sweet juicy pineapples and cherries. It pairs perfectly with the buttery sweet, moist, and slightly dense cake.

I LOVE me some pineapple upside down cake. It’s such a delicious summer bake and it’s so easy to make using a cast iron skillet!

Tips and Tricks

• When making the topping, don’t completely melt the brown sugar in butter. Simply sprinkle it on there and top immediately with pineapple rings and cherries.
• Pat dry pineapple rings and cherries with paper towel before placing it on skillet
• Use a spatula to evenly spread out cake batter after its being poured on skillet. If not evenly spread out, your cake might be slightly lopsided 🙂
• Let skillet pineapple upside down cake cool for 20-30 minutes before flipping it upside down. I typically don’t have issues removing cake from the cast iron skillet due to a buttery topping and the non-stick quality of cast iron skillets.

Frequently Asked Questions

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