This Pineapple Upside-Down Cake is a tender, buttery treat crowned with a glossy layer of caramelized pineapple rings and cherries. Moist, flavorful, and a joy to slice into, it’s the kind of dessert that never goes out of style.

Why You’ll Love This Recipe

If you grew up with the comforting aroma of cakes baking in the kitchen, this recipe will feel like home. It’s sweet but balanced, moist without being heavy, and has that irresistible mix of tangy pineapple, soft vanilla cake, and rich caramel topping. Whether you’re baking for a holiday, Sunday dinner, or just because, this cake delivers nostalgia in every bite.

Classic Pineapple Upside-Down Cake

There’s something about a Pineapple Upside-Down Cake that feels like stepping into a warm kitchen on a Sunday afternoon, where sunlight filters through lace curtains and the air is filled with the scent of baking. It’s a dessert with a story, one that has graced family tables for generations, bringing comfort and cheer in every slice.

This cake holds a special place in the hearts of many because it’s more than just a recipe—it’s a ritual. In decades past, the arrival of a can of pineapple rings in the pantry meant something wonderful was about to happen. Those golden circles promised a treat that was as pleasing to the eye as it was to the taste buds.

Part of the charm comes from the way the topping transforms in the oven. Butter and brown sugar melt together, creating a rich caramel that seeps into the fruit. The pineapple takes on a deep, golden hue, and the cherries glisten like jewels nestled among the rings. It’s a display of simple ingredients creating something extraordinary.

Over the years, cooks have made their own subtle tweaks, and this version builds on that tradition. A hint of vanilla softens the edges of the caramel’s sweetness, while a touch of pineapple juice in the batter keeps the crumb extra moist. These little enhancements ensure that every bite is a balance of flavor and texture.

The cake itself is light yet sturdy, able to hold the topping without becoming soggy. It’s a satisfying contrast: airy cake beneath a dense, syrupy crown of fruit. Baking it in a cast iron skillet not only gives it an even bake but also adds a touch of rustic charm to the presentation.

As it bakes, the kitchen fills with the comforting aroma of sugar, butter, and fruit mingling together. It’s the kind of smell that makes people wander in from other rooms, drawn by an invisible string of sweetness.

Serving the cake is always a little moment of magic. After a brief rest, you flip it onto a plate, revealing the glossy, caramelized topping. The first slice releases a soft sigh of steam, inviting you to dig in while it’s still warm.

This is a cake that doesn’t need frosting, powdered sugar, or elaborate decoration. Its beauty lies in its simplicity, in the honest way the fruit takes center stage. The natural pattern of the pineapple rings and the pop of red from the cherries are decoration enough.

It’s a dessert that feels right at home on a holiday table, yet is just as welcome on a regular Tuesday night. It travels well, making it a perfect choice for potlucks or picnics, and it’s forgiving enough that you can make it ahead without worry.

Leftovers, if you’re lucky enough to have any, keep well for a day or two. But more often than not, the cake disappears quickly, each slice claimed with a smile. It’s the kind of dessert that draws people back for seconds.

Pineapple Upside-Down Cake may be old-fashioned, but it’s far from outdated. In a world of fleeting food trends, it stands as a reminder of the enduring appeal of a well-made classic. It’s proof that the best recipes aren’t always the fanciest—they’re the ones that bring people together.

Servings

8 servings

Time

• Prep Time: 20 minutes
• Cook Time: 35 minutes
• Cooling Time: 5 minutes
• Total Time: 1 hour

Ingredients

• 1 cup sifted cake flour
• 1 teaspoon baking powder
• 1/4 teaspoon salt
• 4 large eggs, separated
• 1 cup white sugar
• 1 teaspoon vanilla extract
• 1 tablespoon butter, melted
• 1/2 cup unsalted butter
• 1 cup packed light brown sugar
• 1 (20-ounce) can sliced pineapple, drained (reserve 3 tablespoons juice)
• 10 maraschino cherries, halved

Instructions

1. Preheat the oven to 325°F (165°C).
2. In a 10-inch cast iron skillet or heavy oven-safe pan, melt 1/2 cup butter over low heat. Remove from heat and sprinkle brown sugar evenly over the melted butter.
3. Arrange pineapple slices over the sugar mixture, fitting them snugly. Place cherry halves in the center of each pineapple ring and in any open spaces.
4. In a medium bowl, sift together cake flour, baking powder, and salt. Set aside.
5. Separate eggs, placing whites in a large mixing bowl and yolks in a smaller bowl.
6. Beat egg whites on medium speed until soft peaks form. Gradually add white sugar, continuing to beat until medium-stiff peaks form.
7. Beat egg yolks until thick and lemon-colored. Gently fold yolks into the whipped egg whites.
8. Sprinkle the flour mixture over the eggs and fold gently until just blended.
9. Stir in vanilla extract, reserved pineapple juice, and 1 tablespoon melted butter.
10. Pour batter evenly over the arranged fruit in the skillet.
11. Bake 30–35 minutes, or until a toothpick inserted in the center comes out clean.
12. Let the cake cool for 5 minutes in the pan. Run a knife around the edges, then carefully invert onto a serving plate.
13. Serve warm or at room temperature.

Tips

• Use room temperature eggs for better volume when whipping.
• A cast iron skillet retains heat beautifully, creating an even caramel layer.
• Drain pineapple well to avoid excess moisture in the cake.
• For an extra glossy finish, lightly brush cherries with melted butter before baking.