Classic Pineapple Upside-Down Cake

Few desserts bring as much nostalgia and sweet caramelized flavor as a Classic Pineapple Upside-Down Cake. This retro favorite, known for its buttery, moist cake and golden pineapple topping, has been a staple in American kitchens for nearly a century.

Unlike traditional cakes, this one is baked with the topping on the bottom, then flipped to reveal a beautiful, glossy pineapple-cherry design. Whether you’re baking for a special occasion or just craving something sweet and tangy, this cake never disappoints.

The History of Pineapple Upside-Down Cake

Did you know that this dessert became famous thanks to a 1925 Dole Pineapple recipe contest? Before that, upside-down cakes were already popular, typically made with seasonal fruits like apples or berries. But when canned pineapple became widely available, it transformed this cake into the iconic treat we know today.

For a deep dive into the origins of this cake, check out this fascinating history.

Essential Ingredients and Their Roles

To achieve a perfectly moist and tender cake, each ingredient plays a crucial role:

Cake flour – Creates a lighter crumb compared to all-purpose flour.
Brown sugar – Caramelizes with the butter to create the signature topping.
Unsalted butter – Adds richness and helps with caramelization.
Egg whites – Keep the cake light while still supporting the topping.
Sour cream or yogurt – Ensures the cake stays moist and fluffy.
Pineapple juice – Enhances the fruity flavor in the cake batter.

If you love fruit-based desserts, you might also enjoy trying a caramel apple éclair cake recipe—a delicious twist on classic flavors.

Step-by-Step Guide to Making a Perfect Pineapple Upside-Down Cake

1. Preparing the Topping

Melt ¼ cup unsalted butter and pour it into a 9-inch round cake pan.
Sprinkle ½ cup packed brown sugar evenly over the butter.
Arrange 8–10 pineapple rings in a single layer. Place maraschino cherries in the center of each ring.
✔️ Tip: Blot the pineapples and cherries with a paper towel to remove excess moisture.

2. Making the Cake Batter

Whisk together:

1½ cups cake flour
1 tsp baking powder
¼ tsp baking soda
½ tsp salt

In a separate bowl, cream together:

6 tbsp softened unsalted butter
¾ cup granulated sugar

Add:

2 large egg whites (room temperature)
⅓ cup sour cream
1 tsp vanilla extract

Slowly mix in:

¼ cup pineapple juice
2 tbsp whole milk

3. Baking the Cake

Pour the batter gently over the pineapple topping.
Bake at 350°F (177°C) for 43-48 minutes.
Tip: Cover loosely with foil after 25 minutes to prevent excessive browning.

4. Flipping the Cake

Let the cake cool for 20 minutes before inverting.
Run a knife around the edges, place a serving plate on top, and flip it quickly but carefully.
Tip: If some fruit sticks to the pan, gently replace it on top of the cake.

Delicious Variations of Pineapple Upside-Down Cake

If you want to put your own spin on this classic, try these fun variations:

Gluten-free version: Use almond flour or gluten-free baking mix.
Dairy-free option: Substitute butter with vegan butter and milk with almond milk.
Fresh pineapple twist: Swap canned pineapple for thin slices of fresh pineapple.
Other fruit toppings: Try peaches, apples, or bananas for a new flavor experience.

Expert Baking Tips for Success

Always blot the pineapple and cherries to prevent a soggy cake.
Use a deep 9-inch cake pan to prevent overflow.
Don’t overmix the batter—this can make the cake dense.
Bake on a middle oven rack for even cooking.

Storage & Reheating Instructions

Short-Term Storage

Keep covered at room temperature for up to 2 days.
If refrigerating, cover tightly to prevent drying out.

Freezing

✔️ Wrap individual slices in plastic wrap and store in an airtight container for up to 3 months.
✔️ Thaw at room temperature before serving.

Reheating

✔️ Microwave slices for 10-15 seconds or warm in a 300°F oven for 5 minutes.

How to Serve Pineapple Upside-Down Cake

Serve warm or at room temperature—the flavors shine best this way.
Pair with vanilla ice cream, whipped cream, or caramel drizzle.
Enjoy with coffee, tea, or a sweet dessert wine for a perfect pairing.

Frequently Asked Questions (FAQs)

❓ Why does my pineapple upside-down cake turn out soggy?
💡 Too much juice! Always blot the fruit before using.

❓ Can I make it the night before?
💡 Yes! Store in an airtight container and reheat before serving.

❓ Should I use fresh or canned pineapple?
💡 Canned is traditional, but fresh pineapple gives a bold, fresh flavor.

❓ How do I prevent the cake from sticking?
💡 Generously grease the pan and let it cool before flipping.

❓ Can I use a boxed cake mix?
💡 Yes! Just use the topping instructions above with any yellow cake mix.

Final Thoughts

A Classic Pineapple Upside-Down Cake is more than just a dessert—it’s a piece of culinary history. With its buttery crumb, caramelized topping, and sweet pineapple flavor, this cake will always have a place at the table.

Try it for your next gathering and experience why this retro classic remains a beloved favorite. And don’t forget to share your baking success in the comments!