Pineapple Upside-Down Cake – Classic Caramelized Pineapple

Pineapple Upside-Down Cake – Few desserts evoke nostalgia and tropical charm quite like the famous Pineapple Upside-Down Cake. This classic treat, known for its glossy caramelized pineapple rings and vibrant maraschino cherries, has remained a beloved staple for generations.

• Save

Unlike traditional cakes baked right-side up, this one boasts a unique technique—baking the fruit at the bottom of the pan beneath a buttery brown sugar topping, which turns into a rich caramel during baking. Once flipped, the fruit layer sits beautifully atop a tender vanilla cake, creating a picture-perfect dessert that’s both delicious and visually stunning.

Recipe Overview

• Cuisine: American

• Course: Dessert, Holiday Cake

• Prep Time: 20 minutes

• Active Time: 20 minutes

• Resting Time: 15 minutes

• Baking Time: 40–45 minutes

• Total Time: 1 hour 20 minutes

• Servings: 10–12 servings

• Calories per Serving: ~390 calories

Nutrition Table (Per Slice)

Ingredients

For the Topping

• ¼ cup unsalted butter (melted)

• ½ cup brown sugar (packed)

• 6–8 pineapple rings (canned or fresh)

• Maraschino cherries (one per pineapple ring)

For the Cake Batter

• 1 ½ cups all-purpose flour

• 1 cup granulated sugar

• ½ cup unsalted butter (softened)

• 2 large eggs (room temperature)

• 1 teaspoon vanilla extract

• 1 ½ teaspoons baking powder

• ¼ teaspoon salt

• ½ cup whole milk

• ¼ cup pineapple juice (from can or fresh)

Equipment Needed

• 9-inch round cake pan or cast-iron skillet

• Mixing bowls

• Hand mixer or stand mixer

• Whisk

• Rubber spatula

• Cooling rack

• Measuring cups and spoons

• Toothpick for testing doneness

Instructions

Step 1: Prepare the Topping

1. Melt the butter and pour it evenly into the bottom of your cake pan.

2. Sprinkle brown sugar over the melted butter, spreading it out to coat the surface.

3. Arrange pineapple rings neatly on top of the butter-sugar mixture.

4. Place a maraschino cherry in the center of each pineapple ring.

5. Set the pan aside.

This layer will caramelize as it bakes, forming the signature glossy top.

Step 2: Prepare the Cake Batter

1. In a medium bowl, whisk together flour, baking powder, and salt.

2. In another bowl, use a mixer to cream the softened butter and granulated sugar until light and fluffy.

3. Add the eggs one at a time, mixing well after each addition.

4. Blend in the vanilla extract.

5. On low speed, alternate adding the dry mixture with milk and pineapple juice until a smooth batter forms.

6. Do not overmix—this keeps the cake soft and tender.

Step 3: Assemble the Cake

1. Pour the cake batter gently over the arranged pineapples in the pan.

2. Use a spatula to smooth the surface without disturbing the fruit layer.

3. Tap the pan lightly on the counter to remove air bubbles.

Step 4: Bake

1. Preheat the oven to 350°F (175°C).

2. Bake the cake for 40–45 minutes, or until golden and springy.

3. Insert a toothpick in the center; it should come out clean.

4. If the top browns too fast, lightly cover with foil.

Step 5: Flip the Cake

1. Let the cake cool in the pan for 15 minutes.

2. Run a knife around the edges to loosen it.

3. Place a serving plate over the pan and flip carefully in one quick motion.

4. Lift the pan slowly to reveal the caramelized pineapple topping.

 Tips for a Perfect Pineapple Upside-Down Cake

1. Use real pineapple juice

It enhances tropical flavor and adds moisture.

2. Avoid overmixing

This keeps the cake light instead of dense.

3. Don’t skip the resting time

It helps the caramel set and prevents the cake from tearing while flipping.

4. Use room-temperature ingredients

This ensures smooth mixing and an even crumb.

5. Make it in a cast-iron skillet

It caramelizes the sugar better for a richer flavor.

6. Add spices for extra depth

Cinnamon or nutmeg pairs wonderfully with pineapple.

Conclusion

A Pineapple Upside-Down Cake is more than just a dessert—it’s a delightful blend of tradition, tropical flavors, and irresistible caramelized sweetness. With its signature pineapple rings, glossy cherry accents, and perfectly soft vanilla cake, this retro classic remains a crowd favorite for good reason. Whether you’re making it for a celebration, a family gathering, or a simple weekend treat, the balance of fruity brightness and buttery richness makes every slice unforgettable.