Pineapple Upside Down Cake

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Golden, glossy, and irresistibly moist, Pineapple Upside Down Cake is the vintage dessert that never goes out of style. The moment you flip the pan and reveal those caramelized pineapple rings studded with cherries, you know you’re about to serve something special. With its tender yellow cake base and buttery brown sugar topping, this cake is both visually stunning and decadently delicious.

Whether you’re making it for a holiday dinner, summer picnic, or just because Tuesday needs something sweet, this cake always delivers. It’s got a comforting old-school charm but feels just right in modern kitchens. Plus, it smells like nostalgia baked with a tropical twist.

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Why You’ll Love This Pineapple Upside Down Cake

• Showstopper looks: Those pineapple rings and cherries make for an eye-catching presentation without any fancy decorating skills.
• One-pan magic: Everything bakes in one pan, so you get your topping and cake in a single flip.
• Perfect balance: The sugary topping is beautifully offset by the light, fluffy cake.
• Classic comfort: This is the kind of dessert that brings smiles and second helpings.

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What Kind of Pineapple Should I Use?

Canned pineapple rings are the traditional and easiest choice. They’re uniform in size, perfectly sweet, and ready to go. Just make sure to drain them well before placing them into your baking pan to avoid a soggy cake base. If you’re using fresh pineapple, slice it into even rings and briefly saute them in butter and sugar for a similar effect.

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Ingredients for the Pineapple Upside Down Cake

Every ingredient in this recipe plays a key role in creating the perfect balance of texture and flavor. Here’s why each one matters:

• Pineapple rings (canned or fresh): They’re the star of the show and bring tangy-sweet flavor.
• Maraschino cherries: Add a pop of color and nostalgic charm.
• Brown sugar: Caramelizes to create a sticky-sweet topping.
• Unsalted butter: Used for both the topping and cake, it adds richness.
• Granulated sugar: Sweetens the cake without overpowering the topping.
• Eggs: Bind the batter and provide structure.
• All-purpose flour: The base of the cake for a tender crumb.
• Baking powder: Helps the cake rise and stay fluffy.
• Salt: Enhances all the sweet flavors.
• Whole milk: Keeps the batter moist and smooth.
• Vanilla extract: Adds warm, fragrant flavor to the cake.

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How To Make the Pineapple Upside Down Cake

Step 1: Prepare the Pan

Grease a 9-inch round cake pan. Melt butter and brown sugar together, then pour into the pan to coat the bottom. Arrange pineapple rings in a single layer over the sugar mixture and place a cherry in the center of each ring.

Step 2: Make the Cake Batter

In a large bowl, cream together the butter and sugar until fluffy. Beat in eggs one at a time. Add vanilla extract. In a separate bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet mixture, alternating with milk.

Step 3: Combine and Bake

Gently pour the batter over the pineapple layer, smoothing the top. Bake at 350°F (175°C) for 40-45 minutes until golden and a toothpick comes out clean.

Step 4: Flip and Cool

Let the cake cool in the pan for 5-10 minutes. Run a knife around the edges, place a plate over the pan, and flip it upside down. Carefully lift the pan to reveal your beautiful pineapple topping.

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How to Serve and Store Pineapple Upside Down Cake

This recipe serves 8 generous slices, making it perfect for gatherings, family desserts, or just a week of sweet snacking. Serve warm with a scoop of vanilla ice cream or chilled for a more caramelized flavor.

Store leftovers covered in the refrigerator for up to 4 days. You can reheat individual slices in the microwave for 10-15 seconds to bring back that gooey warmth. Avoid freezing, as the pineapple topping doesn’t thaw well.

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What to Serve With Pineapple Upside Down Cake?

Vanilla Ice Cream

The cold, creamy texture balances the warm, sticky cake beautifully.

Whipped Cream

A light dollop makes each bite feel even more indulgent.

Coconut Flakes

Sprinkle some toasted coconut for a true tropical treat.

Caramel Drizzle

Double up on that caramel flavor with a warm drizzle over each slice.

Grilled Pineapple

Go all in with pineapple and serve with some grilled pineapple on the side.

Hot Coffee

A robust brew cuts through the sweetness and pairs wonderfully.

Iced Tea with Mint

Perfect for warm days when you want something refreshing.

Rum Sauce

Add a grown-up twist with a buttery rum glaze drizzled over the top.

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Want More Cake Ideas with a Twist?

If you loved this Pineapple Upside Down Cake, you’ll want to try these next:

• Tasty Pineapple Juice Cake – A soft and tropical take on classic bundt.
• Chocolate Raspberry Drip Cake – For when you’re feeling decadent.
• The Ultimate Cinnamon Roll Cheesecake – Cinnamon-sugar lovers, this one’s for you.
• Cherry Chocolate Cheesecake – A stunning pairing of fruit and chocolate.
• Lemon Cake to Die For – Bright, tangy, and perfect for spring.

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📌 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 add coconut? Maybe you gave it a rum twist?

I love seeing how others bring these recipes to life. Feel free to ask questions, share your tweaks, or drop your photos!

Explore beautifully curated health-boosting drinks and desserts on Chef Lorenzo Recipes on Pinterest and discover your new favorite indulgence.

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