Pineapple Upside-Down Cake is a timeless classic that combines caramelized pineapple slices, a rich buttery cake, and a hint of vanilla for a dessert that’s as beautiful as it is delicious. The golden pineapple rings, glazed with a brown sugar and butter topping, create a stunning presentation when flipped after baking. This moist, flavorful cake is perfect for gatherings, holidays, or a comforting homemade treat.

Why You’ll Love This Recipe

Classic and Nostalgic: A retro favorite that never goes out of style.
Caramelized Pineapple Topping: The butter and brown sugar glaze creates a sweet, syrupy finish.
Soft and Moist Cake: A tender vanilla cake that perfectly complements the fruity topping.
Simple to Make: No special techniques required—just layer, bake, and flip!
Perfect for Any Occasion: A great dessert for birthdays, holidays, or casual get-togethers.

Ingredients

(Tip: You can find the complete list of ingredients and their measurements in the recipe card below.)

For the Topping:

¼ cup (60g) unsalted butter, melted
½ cup (100g) brown sugar, packed
7 pineapple rings (canned or fresh)
7 maraschino cherries (optional, for garnish)

For the Cake:

1 ½ cups (190g) all-purpose flour
1 ½ teaspoons baking powder
½ teaspoon salt
½ cup (115g) unsalted butter, softened
¾ cup (150g) granulated sugar
2 large eggs
1 teaspoon vanilla extract
½ cup (120ml) whole milk
¼ cup (60ml) pineapple juice (from the canned pineapples)

Directions

1. Prepare the Topping

Preheat your oven to 350°F (175°C).
Pour the melted butter into a 9-inch round cake pan, spreading it evenly.
Sprinkle the brown sugar over the butter.
Arrange the pineapple rings on top of the brown sugar. Place a maraschino cherry in the center of each pineapple ring.

2. Make the Cake Batter

In a medium bowl, whisk together the flour, baking powder, and salt.
In a separate large bowl, beat the softened butter and granulated sugar until light and fluffy.
Add the eggs one at a time, beating well after each addition. Stir in the vanilla extract.
Gradually mix in the dry ingredients, alternating with the milk and pineapple juice, until fully combined.

3. Assemble and Bake

Pour the cake batter over the pineapple topping, spreading it evenly.
Bake for 35-40 minutes, or until a toothpick inserted into the center comes out clean.
Let the cake cool in the pan for 10 minutes.
Run a knife around the edges, then carefully invert onto a serving plate. Allow the cake to cool before slicing.

Servings and Timing

Servings: 8
Prep Time: 15 minutes
Cook Time: 40 minutes
Cooling Time: 10 minutes
Total Time: 1 hour 5 minutes

Variations

Spiced Version: Add a teaspoon of cinnamon or nutmeg for extra warmth.
Coconut Twist: Replace half of the milk with coconut milk and add shredded coconut to the batter.
Rum-Infused Cake: Add a tablespoon of dark rum to the batter for a tropical kick.
Nutty Crunch: Sprinkle chopped pecans or walnuts over the brown sugar topping before adding the pineapples.
Mini Cakes: Make individual portions by using muffin tins instead of a cake pan.

Storage and Reheating

Refrigeration: Store in an airtight container in the refrigerator for up to 3 days.
Freezing: Wrap slices tightly in plastic wrap and freeze for up to 2 months. Thaw in the fridge before serving.
Reheating: Warm slices in the microwave for 10-15 seconds or in the oven at 300°F (150°C) for a few minutes.

FAQs

Can I use fresh pineapple instead of canned?

Yes! Just slice fresh pineapple into rings and use in place of canned.

What if my cake sticks to the pan?

Let the cake cool for 10 minutes, then run a knife around the edges before flipping. Greasing the pan well also helps.

Can I make this cake ahead of time?

Yes, it can be made a day in advance and stored covered at room temperature or in the fridge.

Can I use a cake mix instead of making it from scratch?

Yes! Prepare a vanilla or yellow cake mix and pour it over the pineapple topping.

How do I prevent the topping from becoming too sticky?

Make sure to let the cake cool for at least 10 minutes before flipping. This allows the caramelized topping to set slightly.

Can I use a different fruit instead of pineapple?

Yes! Try peaches, apples, or pears for a delicious variation.

What’s the best way to serve pineapple upside-down cake?

Enjoy it warm with whipped cream or a scoop of vanilla ice cream.

Can I bake this in a bundt pan?

Yes, but the arrangement of the pineapples will be different. Grease the pan well and adjust the baking time slightly.

How can I make this cake dairy-free?

Use dairy-free butter and substitute the milk with almond or coconut milk.

Why is my cake too dense?

Overmixing the batter can result in a dense cake. Mix just until combined for a light and fluffy texture.

Conclusion

Pineapple Upside-Down Cake is a delightful, vintage dessert that remains a favorite for good reason. With its caramelized pineapple topping and buttery vanilla cake, it’s a simple yet impressive treat for any occasion. Whether you’re making it for a family gathering, holiday, or just because, this cake is sure to be a hit. Try it today and enjoy a slice of sweet, tropical goodness!