Classic Pineapple Upside-Down Cake

I absolutely love making Classic Pineapple Upside-Down Cake because it’s a nostalgic, comforting dessert that always brings a smile to my face. The caramelized pineapple rings paired with the buttery, fluffy cake create the perfect balance of sweetness and texture. The brown sugar and butter caramelize together to form a rich, golden syrup that soaks into the cake, giving it an irresistible flavor. It’s the kind of cake that’s perfect for any occasion, whether it’s a family dinner or a sweet treat for yourself!

Why I’ll Love This Recipe

What I love most about this cake is how the pineapple slices get wonderfully caramelized in the oven, and when flipped, they reveal a beautiful, glistening topping. The cake itself is light and moist, and the combination of the tropical pineapple with the buttery brown sugar topping is always a crowd-pleaser. It’s not overly complicated, but the result is a showstopper that feels elegant and homemade.

Ingredients

(Hear’s a tip: Check out the full list of ingredients and measurements in the recipe card below.)

For the Topping:

• 1/4 cup unsalted butter

• 1/2 cup packed brown sugar

• 6-8 pineapple rings (canned or fresh)

• Maraschino cherries (optional, for garnish)

For the Cake:

• 1 1/2 cups all-purpose flour

• 1 1/2 teaspoons baking powder

• 1/4 teaspoon salt

• 1/2 cup unsalted butter, softened

• 1 cup granulated sugar

• 2 large eggs

• 1 teaspoon vanilla extract

• 1/2 cup whole milk

• 1/4 cup pineapple juice (from the can of pineapple rings)

Directions

1. Preheat the Oven:
   First, I preheat the oven to 350°F (175°C). I grease a 9-inch round cake pan and set it aside.

2. Make the Topping:
   In a small saucepan, I melt the butter over medium heat. Once melted, I stir in the brown sugar and cook for 1-2 minutes until the mixture becomes bubbly and smooth.
   I pour this mixture into the bottom of the prepared cake pan, spreading it evenly. Then, I arrange the pineapple rings on top, making sure to place one in the center and the rest around it. If I want to add a touch of color, I place a maraschino cherry in the center of each pineapple ring.

3. Prepare the Cake Batter:
   In a medium bowl, I whisk together the flour, baking powder, and salt.
   In a large mixing bowl, I cream the softened butter and granulated sugar together until light and fluffy, about 3 minutes.
   I add the eggs, one at a time, mixing well after each addition, followed by the vanilla extract.
   I alternate adding the dry ingredients and the milk, starting and ending with the dry ingredients, mixing until just combined. I finish by stirring in the pineapple juice to bring everything together.

4. Assemble and Bake the Cake:
   I gently pour the cake batter over the pineapple rings in the prepared pan, spreading it evenly with a spatula.
   I bake the cake for 30-35 minutes, or until a toothpick inserted into the center comes out clean and the cake is golden brown.

5. Flip the Cake:
   Once the cake is done baking, I let it cool in the pan for about 5 minutes. Then, I carefully run a knife around the edges of the cake to loosen it.
   I place a serving plate over the top of the pan and flip it over quickly. The cake should come out easily with the caramelized pineapple topping facing up. I let the cake cool for another 10-15 minutes before serving.

6. Serve:
   Once the cake has cooled slightly, I slice it and serve! The caramelized pineapple and sweet syrup make this cake a real treat.

Servings and Timing

This recipe yields about 8-10 servings. Prep time is around 15 minutes, and baking time is about 30-35 minutes. Total time is about 1 hour (including cooling).

Variations

I like to change it up by:

• Adding other fruits: You can use peaches, cherries, or even bananas in place of the pineapple for a fun twist.

• Using brown butter for the topping to add a nutty flavor.

• Sprinkling cinnamon on the batter for a warm, spiced flavor that complements the pineapple.

• Making mini versions: This cake can be made in individual ramekins or muffin tins for single-serving portions.

Storage / Reheating

I store any leftover cake in an airtight container at room temperature for up to 3 days. I can also refrigerate it for up to 5 days, but it’s best served at room temperature or slightly warmed. I recommend reheating it in the microwave for 10-15 seconds to soften it and bring back that delicious caramelized topping.

FAQs

1. Can I use fresh pineapple instead of canned?
   Yes! You can use fresh pineapple rings, but be sure to remove the core and slice them evenly. The fresh fruit will be just as delicious and juicy.

2. Can I make this cake ahead of time?
   Yes! This cake can be made a day ahead of time, and it actually gets better as the flavors settle. Just store it at room temperature and cover it tightly.

3. Can I add coconut to this cake?
   Yes! Adding shredded coconut to the batter or sprinkling it on top of the cake will add a tropical flair that pairs perfectly with the pineapple.

4. Is this cake gluten-free?
   Unfortunately, this cake is not gluten-free. However, you could try substituting a gluten-free flour blend to make it suitable for those with gluten sensitivities.

5. Can I freeze this cake?
   Yes, this cake freezes well. I recommend freezing the cake without the pineapple topping first, then adding the topping once you defrost it.

Conclusion

Classic Pineapple Upside-Down Cake is a timeless dessert that never goes out of style. The caramelized pineapple and brown sugar topping create a rich, syrupy sweetness that soaks into the soft, buttery cake. It’s a comforting and nostalgic treat that’s perfect for any gathering or just as a sweet indulgence. Whether it’s a special occasion or a casual family dessert, this cake is sure to impress with its delicious flavors and beautiful presentation.