Homemade Pineapple Upside-Down Cake

Homemade Pineapple Upside-Down Cake

Baking a pineapple upside-down cake is a right of passage for all cast iron skillet users and is a great recipe to try after you've had a chance to break in your new Lancaster Skillet. Pineapple is an acidic food so, it is a good idea to only bake a pineapple upside down cake in a well-seasoned skillet.

Growing up in Pennsylvania, my mom would traditionally make pineapple upside down cake on cold winter evenings. If you've ever tried one before, you know that the best time to slice and eat is about 20 minutes after it's been pulled out of the oven and flipped. The warm moist texture is irresistible.

Speaking of flipping, the best part of baking this cake is the satisfaction you receive by inverting your cast iron skillet (with a plate placed over the top of the skillet) and revealing a perfectly formed cake with warm buttery brown sugar icing. 

I was looking for a relatively quick pineapple upside down cake recipe to make from scratch, and my friend, Lucy Vaserfirer, had one that fit the bill perfectly. Her recipe only takes an hour from the oven preheat to the dessert plate. I decided to share her recipe here, but I would recommend checking out many more creative and delicious recipes in her cookbook: Not Your Mother's Cast Iron Skillet Cookbook.

Pineapple Upside Down Cake Recipe


No. 8 Lancaster skillet or similar 10.5-inch skillet

Hand Mixer


1-1/2 cups all-purpose flour

1-1/2 teaspoon baking powder

1/2 teaspoon kosher salt

8 tablespoons unsalted butter

1/2 cup packed light brown sugar

1 small pineapple peeled, sliced and cored OR 1 can of pineapple rings

Maraschino cherries

3/4 cup white sugar

2 eggs

1-1/2 teaspoons vanilla extract

1/2 cup pineapple juice


 1. Preheat your oven to 350°F.

2. Mix the flour, baking powder and kosher salt in a mixing bowl.

3. Melt 2 tablespoons of butter in your cast iron skillet on the stovetop over low heat. Remove the skillet after the butter is melted, and coat all interior surfaces of the pan. Spread the brown sugar evenly over the bottom of the skillet. Place pineapple rings throughout the bottom of the skillet, and add maraschino cherries to the center of each ring.

4. Using a mixer, beat the remaining 6 tablespoons of softened butter and sugar for several minutes. Add the vanilla extract and eggs, one at a time, beating continuously until well mixed. Gradually add in the dry ingredients and pineapple juice, mixing continuously.

5. Pour the batter into the skillet, spreading it evenly over the pineapple and cherries. Be careful to not disturb the fruit while transferring the batter. Bake for 45-50 minutes.

6. Use the toothpick method to confirm that the pineapple upside down cake is fully baked and allow to cool for 10 minutes. Place a cake plate over the skillet before flipping to unmold the cake. Allowing the cake to cool for too long before flipping may cause the cake to stick.

Used by permission of the Quarto Publishing Group.