I love making pineapple upside down cake in a cast iron skillet because the skillet gives the cake a beautiful golden crust and ensures even baking. The caramelized pineapple rings and cherries on top aren’t just stunning; they also keep the cake moist and flavorful. This old-fashioned dessert is nostalgic, simple, and always a hit whether I make it for a family dinner or a summer holiday gathering.
Pineapple Upside Down Cake in a Cast Iron Skillet
For me, the magic of a cast iron pineapple upside down cake is in the flip. Watching the caramelized topping slide perfectly onto the cake plate is always a showstopper. I love that this dessert is “all-in-one”–no frosting needed, and the fruit is perfectly baked into the cake. I usually make it with pantry staples: canned pineapple rings, maraschino cherries, and simple cake ingredients. It’s my go-to for holidays like the 4th of July or Labor Day because it’s easy, yet impressive.
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The Secret to a Clean Flip
This homemade pineapple upside down cake is and always will be on the denser side compared to more traditional cakes due to the moist fruit. The fruit will begin to weigh down the cake as soon as you flip it, making the crumb denser as it sits. It’s important to make sure the cake has fully baked through before flipping!
Skillet Pineapple Upside Down Cake Recipe
Equipment
- Kitchen Scale (optional)
- 10-inch Cast Iron Skillet
- Hand Mixer
Ingredients
For the Pineapple Top
- 20 ounces canned pineapple rings juice reserved (1 can)*
- 5 tablespoons unsalted butter (⅝ stick)
- 1 cup brown sugar
- 7 maraschino cherries
For the Cake
- 1½ cups all-purpose flour
- 2 teaspoons baking powder
- ¼ teaspoon kosher salt
- ⅔ cup brown sugar
- ½ cup unsalted butter room temperature (1 stick)
- 2 large eggs room temperature
- 2 teaspoons pure vanilla extract
- ½ cup reserved pineapple juice (from above)
Instructions
- Preheat oven to 350°F.
- Drain juice from canned pineapple into a measuring cup. Add water if needed to measure 1 cup. Set aside juice and 7 pineapple rings for the cake. Set any remaining juice and rings aside for another use.20 ounces canned pineapple rings
- Melt butter in a 10-inch cast iron skillet set over medium-high heat.5 tablespoons unsalted butter
- Remove the skillet from the heat and sprinkle brown sugar evenly over the top until all butter is covered.1 cup brown sugar
- Arrange 6 pineapple rings around the outer edge of the skillet and the remaining ring in the center without overlapping. Place a cherry in the center of each pineapple ring.7 maraschino cherries
- In a medium bowl, combine the flour, baking powder, and salt and set aside.1½ cups all-purpose flour, 2 teaspoons baking powder, ¼ teaspoon kosher salt
- In a separate medium bowl, combine brown sugar and softened butter. Using a hand mixer, beat for 2 minutes on medium speed until creamy.⅔ cup brown sugar, ½ cup unsalted butter
- Scrape down the bowl, then add the eggs one at a time, until well mixed. Stir in vanilla.2 large eggs, 2 teaspoons pure vanilla extract
- Gradually add flour mixture alternately with pineapple juice, beating at low speed and scraping the bowl often after each addition.½ cup reserved pineapple juice
- Pour the cake batter over the pineapple rings and spread it into an even layer.
- Bake for 30-40 minutes, or until the middle is set and a toothpick inserted into the cake comes out clean.
- Remove the cake from the oven and allow it to cool for 8-10 minutes, then run a knife or offset spatula around the edges to gently loosen the cake.
- Set a plate over the skillet, then flip and carefully turn the warm cake out onto a plate. Transfer any fruit or glaze that sticks in the skillet back to the cake. Serve with whipped cream.
Notes
- If you don’t have a 10-inch skillet, you can adjust for an 8- or 9-inch skillet–just slightly reduce baking time to avoid overbrowning.
- Make sure the butter and sugar are evenly melted and spread across the skillet to prevent uneven caramelization or hot spots.
- Pat the fruits dry to avoid a soggy cake, and if they’re slippery, chill the rings for a few minutes so they stay in place.
- Take care not to overmix the cake batter, or the cake will turn out dry.
- Don’t press too hard when spreading the batter over the fruit, or you risk dislodging it.
- Because the cake is dense and wet from pineapple, check that the edges are pulling away from the pan slightly and that the center springs back to the touch, in addition to the toothpick test.
- This cake does tend to turn out quite dark; tent the pan with foil to prevent over browning if desired.
- Don’t leave the cake in the pan for too long; otherwise, it could get stuck.
- Use a plate or cake board that’s slightly larger than the skillet and flip in one smooth motion to keep the design intact.
- Brush the finished cake with corn syrup or apricot jam to create a shiny top.
- Warm slightly before serving and top with whipped cream or vanilla ice cream for the best presentation and taste.
Why I Use a Cast Iron Skillet
I always make my pineapple upside down cake in a cast iron skillet because it heats evenly and stays hot, which helps the brown sugar and butter caramelize into that glossy, golden topping. The weight of the skillet also makes the flip super reliable–everything slides out in one beautiful piece.
If you don’t have a cast iron skillet, you can still make a pineapple upside down cake from scratch in a metal cake pan. Just melt the butter and brown sugar on the stovetop first, pour it into the pan, and build the topping as directed. Avoid glass dishes; they heat unevenly and can cause the fruit layer to over-brown or the cake to bake inconsistently.
How to Make Pineapple Upside Down Cake in a Cast Iron Skillet Step-by-Step
Prep: Preheat your oven to 350°F. Bring the butter and eggs to room temperature for 30-60 minutes before beginning. Drain the juice from a 20-ounce can of pineapple into a measuring cup. Add water if needed to measure 1 cup total. Set aside the juice and 7 pineapple rings for the cake. Set any remaining juice and rings aside for another use.
Melt the Butter: Melt 5 tablespoons of unsalted butter in a 10-inch cast iron skillet set over medium-high heat. Make sure the butter covers every inch of the pan to prevent sticking!
Sprinkle the Sugar: Remove the skillet from the heat and sprinkle 1 cup of brown sugar evenly over the top until all butter is covered. Again, make sure it’s all over the pan.
Arrange the Fruit: Arrange 6 pineapple rings around the outer edge of the skillet and the remaining ring in the center without overlapping. Place a maraschino cherry in the center of each pineapple ring (7 total). I like to pat the fruits dry if they feel soggy so they don’t make the cake soggy. You can also briefly chill them so they don’t slide around as much in the pan.
Whisk the Dry Ingredients: In a medium bowl, combine 1½ cups of all-purpose flour, 2 teaspoons of baking powder, and ¼ teaspoon of kosher salt and set aside.
Cream the Butter and Sugar: In a separate medium bowl, combine ⅔ cup of brown sugar and ½ cup of room temperature unsalted butter. Using a hand mixer, beat for 2 minutes on medium speed until creamy.
Add the Eggs and Vanilla: Scrape down the bowl, then add 2 large eggs one at a time, until well mixed. Stir in 2 teaspoons of vanilla extract.
Combine the Batter: Gradually add the flour mixture alternately with ½ cup of reserved pineapple juice, beating at low speed and scraping the bowl often after each addition. Take care not to overmix at this point, or the cake will turn out dense and dry.
Fill the Pan: Pour the cake batter gently over the pineapple rings and spread it into an even layer. Don’t press too hard while spreading, or you’ll move the rings.
Bake the Cake: Bake in the preheated oven for 30-40 minutes, or until the middle is set and a toothpick inserted into the cake comes out clean. You’ll know it’s done when the edges are pulling away from the sides of the pan and the center springs back lightly to the touch. It’s okay. if it’s on the dark side, but you can also tent with foil to prevent it from browning too much.
Unmold the Cake: Remove the cake from the oven and allow it to cool for 8-10 minutes, then run a knife or offset spatula around the edges to gently loosen the cake. Set a large plate over the skillet, then flip and carefully turn the pineapple cake upside down onto a plate. Transfer any fruit or glaze that sticks in the skillet back to the cake. Serve cake slices with whipped cream.
How to Store and Freeze
Store leftover skillet pineapple upside down cake in an airtight container in the refrigerator for up to 5 days or in the freezer tightly wrapped in 2 layers of plastic wrap and 1 layer of aluminum foil for up to 3 months. Let thaw overnight in the refrigerator before enjoying cold or at room temperature.
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