Classic Pineapple Upside Down Cake

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Moist, sweet, and glowing with caramelized pineapple rings and vibrant cherries, this Classic Pineapple Upside Down Cake is a retro dessert that never goes out of style. It flips beautifully out of the pan, revealing a stunning glaze of brown sugar and butter, perfectly nestled under golden pineapple slices. Whether you’re baking for a gathering or just want a cozy treat, this cake brings both charm and satisfaction.

This recipe uses everyday pantry ingredients and canned pineapple slices, making it as convenient as it is impressive. It balances rich, buttery flavor with tropical brightness, and its eye-catching presentation makes it feel like a special occasion cake, even if it’s a Tuesday.

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Why You’ll Love This Classic Pineapple Upside Down Cake

• Foolproof and beginner-friendly: No complicated layering or frosting.
• Visually stunning: A natural centerpiece with vibrant fruit.
• Nostalgic: Classic flavors that take you back.
• Perfect texture: Soft, moist crumb meets gooey caramel topping.

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What Kind of Pineapple Should I Use?

Canned pineapple slices work best for uniform shape and size, and they’re easy to layer perfectly in your pan. Just make sure to pat them dry before using to avoid excess moisture in the cake. You can use fresh pineapple, but ensure it’s sliced evenly and not too thick. For extra flair, don’t forget the maraschino cherries – they complete the iconic look!

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Ingredients for the Classic Pineapple Upside Down Cake

Every ingredient plays a role in creating the texture and flavor of this timeless dessert.

• 1/4 cup unsalted butter: Melted to coat the bottom of the pan, forming the rich caramel base.
• 2/3 cup packed brown sugar: Adds deep, molasses-like sweetness that caramelizes beautifully.
• 7 canned pineapple slices: Drained and dried, they create the classic pattern on top.
• 7 maraschino cherries: For that signature pop of red in the center of each pineapple ring.
• 1 1/2 cups all-purpose flour: Provides structure without being too dense.
• 2 teaspoons baking powder: Ensures the cake rises light and fluffy.
• 1/4 teaspoon salt: Balances the sweetness.
• 1/2 cup unsalted butter, softened: Adds richness and flavor to the batter.
• 1 cup granulated sugar: Sweetens the cake just right.
• 2 large eggs: Bind the ingredients and give structure.
• 1 teaspoon vanilla extract: Enhances the overall flavor.
• 1/2 cup whole milk: Moistens the batter and keeps the crumb tender.

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How To Make the Classic Pineapple Upside Down Cake

Step 1: Prepare the Pan and Fruit

Preheat your oven to 350°F (175°C). In a 9-inch round cake pan, pour in the melted 1/4 cup butter and evenly sprinkle the brown sugar over it. Lay down the pineapple slices in a circular pattern, placing one in the center and six around it. Press a maraschino cherry into the center of each slice.

Step 2: Mix the Dry Ingredients

In a medium bowl, whisk together the flour, baking powder, and salt. Set aside.

Step 3: Cream the Butter and Sugar

In a large bowl, cream together 1/2 cup softened butter and 1 cup granulated sugar until light and fluffy, about 3-4 minutes.

Step 4: Add Eggs and Vanilla

Beat in the eggs, one at a time, followed by the vanilla extract. Mix until well incorporated.

Step 5: Combine Wet and Dry

Add the flour mixture in three parts, alternating with the milk, starting and ending with the flour. Mix until just combined.

Step 6: Pour and Bake

Carefully pour the batter over the arranged fruit in the cake pan. Smooth the top with a spatula. Bake for 45-50 minutes, or until a toothpick inserted in the center comes out clean.

Step 7: Invert and Cool

Let the cake cool in the pan for 10 minutes. Then run a knife around the edges and invert it onto a serving plate. Let cool completely before slicing.

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How to Serve and Store Classic Pineapple Upside Down Cake

This cake yields one 9-inch round cake and serves 8 people generously.

Serve it slightly warm or at room temperature. It pairs wonderfully with a scoop of vanilla ice cream or a dollop of whipped cream.

To store, cover loosely and keep at room temperature for up to 2 days. For longer storage, refrigerate up to 5 days. Reheat slices in the microwave for a just-baked feel.

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What to Serve With Classic Pineapple Upside Down Cake

Whipped Cream or Coconut Whipped Cream

Light and airy, it balances the richness of the caramelized top.

Vanilla Ice Cream

The contrast of cold and warm is a classic treat.

Tropical Fruit Salad

Brighten up your plate with something fresh and zesty like this Tropical Fruit Salad with Honey Lime Dressing.

Iced Coffee or Latte

A lightly sweetened coffee drink complements the flavors perfectly.

Lemon Cupcakes

If you’re serving a dessert spread, these Lemon Cupcakes are bright and zesty companions.

Peach Raspberry Macarons

Delicate and fruity, these Peach Raspberry Macarons add a sophisticated bite.

Cream Cheese Stuffed Peppers

Looking to balance sweet with savory? These Easy Cream Cheese Stuffed Peppers are a great party pairing.

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Frequently Asked Questions

Can I use fresh pineapple instead of canned?

Yes! Just slice it thin and remove the core. Make sure to pat the slices dry to avoid extra moisture in the batter.

Why did my cake stick to the pan?

Make sure to generously grease your pan and allow the cake to cool for at least 10 minutes before flipping. Using parchment paper can help too.

Can I make this in advance?

Absolutely. Bake the cake a day ahead and store it covered at room temperature. It actually tastes even better the next day as the flavors meld.

Can I use a different fruit?

You can try sliced peaches, pears, or even mango! Just keep the fruit layer thin and dry to prevent sogginess.

Can I freeze Pineapple Upside Down Cake?

Yes. Once completely cooled, wrap it tightly in plastic wrap and foil. Freeze for up to 2 months. Thaw overnight and warm before serving.

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Save This Pin For Later

📌 Save this recipe to your Pinterest dessert board so you can come back to it any time.
And let me know in the comments how yours turned out. Did you use fresh pineapple or stick with canned? Did you sneak in some coconut?

I love hearing how others make these recipes their own. Questions are welcome too, let’s help each other bake smarter.

Explore more delicious ideas over on my Pinterest at Meals We Share.

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Conclusion

There’s something undeniably satisfying about flipping a Pineapple Upside Down Cake out of the pan and seeing that glossy, fruit-studded top. This cake is as fun to make as it is to eat, and it’s a dependable crowd-pleaser. With simple ingredients and timeless flavor, it’s no wonder this dessert remains a beloved classic. Make it for brunch, a holiday table, or just to brighten a weekday. You won’t be disappointed.

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