I didn’t know pineapple upside down cake was supposed to be made in a cast iron skillet until I was in my thirties. My mom always baked hers in a regular cake pan, and it turned out fine. But then I watched my neighbor make one in her old cast iron, and I couldn’t believe the difference.

The cast iron creates this perfect caramelized crust on the bottom that becomes the top when you flip it. Plus, you can make the whole thing start to finish in one pan—no transferring sticky pineapple topping or washing extra dishes. Once you try it this way, you’ll never go back to a regular cake pan.

pineapple upside down cake in cast iron skillet — Image: mollyshomeguide.com / Photographer Molly

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Why You’ll Love This Pineapple Upside Down Cake

Cast iron skillet cooking – Using a cast iron skillet gives you that perfect caramelized bottom and crispy edges that you just can’t get with a regular cake pan.
Simple ingredients – This recipe uses pantry staples and canned pineapple, so you don’t need to hunt down any fancy ingredients to make this classic dessert.
Impressive presentation – When you flip this cake over, the beautiful pineapple rings and cherries on top make it look like you spent hours decorating, but it’s actually super easy.
Perfect for sharing – This cake serves a crowd and always gets compliments at potlucks, family dinners, or any time you want to bring a homemade dessert that feels special.
One-pan convenience – You can make the topping and bake the cake all in the same skillet, which means less cleanup and more time to enjoy your dessert.

What Kind of Pineapple Should I Use?

For this classic upside-down cake, canned pineapple rings are really your best bet since they hold their shape beautifully and come with that sweet juice you’ll need for the recipe. You can choose between pineapple packed in juice or syrup – both work well, though juice-packed tends to be a bit less sweet if you prefer a more balanced flavor. Fresh pineapple rings can work too, but they tend to release more moisture during baking and might make your cake a bit soggy. If you do go the fresh route, make sure to cut your rings about 1/2 inch thick and pat them dry with paper towels before arranging them in the skillet.

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Options for Substitutions

This classic cake is pretty forgiving when it comes to swaps, so here are some options if you need to make substitutions:

Buttermilk: No buttermilk? Mix 1 cup regular milk with 1 tablespoon lemon juice or white vinegar and let it sit for 5 minutes. You can also use plain yogurt thinned with a little milk.
Canned pineapple rings: Fresh pineapple works great too – just cut it into rings about ½ inch thick. You’ll need to create your own ‘juice’ by mixing ¼ cup water with 2 tablespoons sugar for the topping.
Dark brown sugar: Light brown sugar works fine for the topping, or you can make your own dark brown sugar by mixing 1 cup white sugar with 2 tablespoons molasses.
Cast iron skillet: Don’t have cast iron? A 9-inch round cake pan works, but you’ll need to melt the butter and sugar mixture on the stovetop first, then pour it into your greased pan.
Maraschino cherries: These are totally optional, but if you want color without the artificial taste, try fresh cranberries or even small pieces of fresh strawberry.
All-purpose flour: Cake flour will give you a more tender crumb – use 1⅔ cups cake flour instead of the all-purpose flour.

Watch Out for These Mistakes While Baking

The biggest mistake when making pineapple upside down cake is not getting your cast iron skillet hot enough before adding the butter and brown sugar – this creates the caramelized base that makes the cake special, so let that skillet heat up on the stovetop first.

Another common error is using too much pineapple juice, which can make your cake soggy and prevent proper caramelization, so drain those pineapple rings well and pat them dry with paper towels before arranging them in the skillet.

Don’t rush the cooling process either – let the cake cool for exactly 5-10 minutes before flipping it out of the pan, as waiting too long will cause the topping to stick, but flipping too soon means everything will slide off.

Finally, make sure your batter isn’t overmixed, which can lead to a tough cake that won’t complement that beautiful caramelized pineapple topping.

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What to Serve With Pineapple Upside Down Cake?

This sweet and fruity cake is pretty perfect on its own, but a scoop of vanilla ice cream on the side makes it even better – especially when the cake is still warm from the oven! The cool, creamy ice cream pairs beautifully with the caramelized pineapple and brown sugar topping. If you want to get a little fancy, try serving it with some freshly whipped cream or even a dollop of mascarpone cheese for extra richness. A hot cup of coffee or black tea also makes a great companion to balance out all that sweetness.

Storage Instructions

Keep Fresh: This pineapple upside down cake stays moist and delicious when covered tightly with plastic wrap or foil at room temperature for up to 3 days. You can also store it in the fridge for up to a week, though I think it tastes best at room temperature. The cast iron skillet actually helps keep it fresh longer than other pans!

Freeze: Want to save some for later? Wrap individual slices in plastic wrap and then place them in a freezer bag for up to 3 months. You can also freeze the whole cake by wrapping it well in plastic wrap and then aluminum foil.

Serve: If you’ve stored it in the fridge, just let it sit at room temperature for about 30 minutes before serving. Frozen slices can be thawed overnight in the fridge or at room temperature for a couple hours. A quick 10-15 seconds in the microwave can warm it up nicely too!

Preparation Time	15-20 minutes
Cooking Time	45-50 minutes
Total Time	60-70 minutes
Level of Difficulty	Medium

Estimated Nutrition

Estimated nutrition for the whole recipe (without optional ingredients):

Calories: 2300-2500
Protein: 18-22 g
Fat: 75-85 g
Carbohydrates: 390-420 g

Ingredients

For the pineapple topping:

4 tbsp butter
1 can (18 to 20 oz) pineapple slices, reserve juice
1/2 cup golden barrel dark brown sugar
Maraschino cherries (optional)

For the cake batter:

4 tbsp cold butter
1 cup golden barrel light brown sugar
2 eggs
1 cup buttermilk
1 tsp vanilla extract
1 1/2 cups all-purpose flour
1 1/2 tsp baking powder
1/2 tsp salt

Step 1: Prepare the Pineapple Topping

4 tbsp butter
1 can (18 to 20 oz) pineapple slices, reserve juice
1/2 cup Golden Barrel dark brown sugar
maraschino cherries (optional)

Preheat the oven to 350°F (175°C).

Meanwhile, heat an 8-inch cast iron skillet over medium-high heat.

Add 4 tablespoons butter to the skillet, followed by the reserved juice from the can of pineapple slices and 1/2 cup Golden Barrel dark brown sugar.

Stir the mixture continuously until the liquid boils and starts to thicken, which should take about 5-7 minutes.

Remove the skillet from the heat and carefully arrange the pineapple rings in the thickened syrup, working from the outside in.

If desired, you can place maraschino cherries in the center of each pineapple ring for a classic touch.

Place the skillet with the arranged pineapple rings in the oven while you prepare the cake batter.

Step 2: Cream Butter and Sugar for the Cake Batter

4 tbsp cold butter
1 cup Golden Barrel light brown sugar
2 eggs
1 tsp vanilla extract

In a large mixing bowl attached to a stand mixer, or using a hand mixer, beat 4 tablespoons cold butter and 1 cup Golden Barrel light brown sugar together until the mixture is light and creamy.

I like to beat the butter for a full minute before adding the sugar—it gives the cake a finer crumb.

Add in the eggs one at a time, then mix in the vanilla extract, ensuring everything is well combined.

Step 3: Combine Dry Ingredients and Finish Cake Batter

1 1/2 cups all-purpose flour
1 1/2 tsp baking powder
1/2 tsp salt
1 cup buttermilk

In a separate small bowl, whisk together 1 1/2 cups all-purpose flour, 1 1/2 teaspoons baking powder, and 1/2 teaspoon salt until evenly combined.

With the mixer on low speed, alternately add the dry ingredients and the buttermilk to the creamed butter mixture, starting and ending with the dry ingredients.

Mix until just combined, being careful not to overmix the batter to keep the cake tender.

Step 4: Assemble and Bake the Pineapple Upside-Down Cake

pineapple and syrup base from Step 1
cake batter from Step 3

Carefully remove the hot skillet with the pineapple rings from the oven.

Pour the prepared cake batter from Step 3 evenly over the arranged pineapples and syrup.

Spread the batter gently to cover all the fruit.

Place the skillet back in the oven and bake for about 45 minutes, or until the cake is golden and a toothpick inserted into the center comes out clean.

To keep the cake extra moist, I sometimes cover the skillet loosely with foil during the last 10 minutes if it starts to brown too quickly.

Step 5: Invert and Cool the Cake

Remove the skillet from the oven and let the cake cool for 10 minutes.

Place a large plate or platter (that is wider than the skillet) over the top of the skillet, then quickly and carefully invert the cake onto the plate.

If any pineapple rings or syrup stick to the skillet, simply remove them and arrange on top of the cake.

I find letting the cake cool a bit before inverting helps keep the topping from running off.