Pineapple Upside Down Cake

Pineapple upside down cake is one of those desserts that feels like a time machine — one slice and I am instantly transported to my grandmother’s kitchen. But do not let the retro vibes fool you because this cake is genuinely delicious and it makes such a statement when you flip it out of the pan and reveal that gorgeous caramelized pineapple topping. People always gasp a little and I am here for it every single time.

The secret to the best pineapple upside down cake is baking it in a cast iron skillet. The cast iron gets the caramel beautifully golden and creates perfectly crisp edges while keeping the cake itself moist and tender. I have been using a 10-inch cast iron skillet from Amazon for years and it is honestly one of my most-used kitchen items. This cake is just one of a hundred reasons to own one. (Affiliate link — I earn a small commission, thank you!)

The Caramelized Topping

The magic of this cake is that the topping bakes right into the bottom of the pan and then becomes the showstopping top when you flip it. Butter and brown sugar melt together in the skillet to form a rich caramel that the pineapple rings soak right into. The cherries in the center of each ring are classic and non-negotiable in my house — they add a pop of color and a little sweet tartness that balances the rich caramel perfectly.

Pineapple Upside Down Cake

A classic pineapple upside down cake with a gorgeous caramelized pineapple and cherry topping baked right into a golden buttery cake — showstopping and simple.

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Prep Time 15 minutes mins

Cook Time 45 minutes mins

Total Time 1 hour hr

Servings: 8 slices

Course: Dessert

Cuisine: American

Ingredients Method Notes

Ingredients

  

• 4 tablespoons unsalted butter for the topping
• 2/3 cup packed brown sugar
• 1 can pineapple rings in juice 20 oz, drained, juice reserved
• 8 maraschino cherries
• 1 1/2 cups all-purpose flour
• 1 1/2 teaspoons baking powder
• 1/4 teaspoon salt
• 1/2 cup unsalted butter softened, for cake
• 3/4 cup granulated sugar
• 2 large eggs
• 1 teaspoon vanilla extract
• 1/2 cup pineapple juice reserved from can

Method

 

1. Preheat oven to 350F. Melt 4 tablespoons butter in a 10-inch cast iron skillet over medium heat. Add brown sugar and stir until dissolved, about 2 minutes. Remove from heat.
2. Arrange pineapple rings in the brown sugar mixture. Place a cherry in the center of each ring and in gaps between rings.
3. Whisk together flour, baking powder, and salt. In a separate bowl, beat butter and granulated sugar until fluffy. Add eggs one at a time, then vanilla.
4. Alternately add flour mixture and pineapple juice to the butter mixture, beginning and ending with flour. Mix just until combined.
5. Pour batter over the pineapple layer in the skillet. Bake 40 to 45 minutes until a toothpick comes out clean.
6. Let cool in pan 10 minutes, then carefully invert onto a serving plate. Serve warm.

Notes

A cast iron skillet is ideal for this recipe — it creates perfectly caramelized edges and conducts heat evenly. This is the cast iron skillet I use and love: https://www.amazon.com/s?k=cast+iron+skillet+10+inch&tag=sideofglam-20

Tips for the Perfect Flip

Let the cake cool in the pan for exactly 10 minutes before inverting — not longer or the caramel will start to set and stick. Place your serving plate over the skillet, hold both firmly together, and flip in one confident motion. Give the pan a gentle tap if needed. Run a butter knife around the edges first if you are nervous. The whole thing should release cleanly onto the plate with all that beautiful caramelized topping intact.

This cake is best served slightly warm, maybe with a scoop of vanilla ice cream or a dollop of fresh whipped cream. It keeps well covered at room temperature for 2 days or in the fridge for up to 4 days. Warm individual slices in the microwave for about 20 seconds to revive that fresh-from-the-oven magic.

A Classic That Never Gets Old

Whether you are making this for a summer gathering, a potluck, or just because you want something beautiful and delicious on a Sunday afternoon, this pineapple upside down cake delivers every single time. It is the kind of dessert that earns compliments even from people who say they do not like pineapple. Make it once and you will understand.

xo, Pam