This pineapple upside down cake brings together the caramelized sweetness of pineapple rings and cherries with a moist, fruity cake base. It’s a dessert that reminds me of Sunday gatherings at my grandmother’s house—simple yet impressive when that moment of flipping the cake reveals the glistening fruit pattern.

Why This Recipe Shines

• Uses both crushed pineapple and rings for maximum fruit flavor throughout
• The cake stays incredibly moist thanks to the pineapple juice in the batter
• No complicated techniques—just mix, arrange, bake, and flip
• That dramatic reveal moment never gets old, even after dozens of bakes
• Versatile enough for both casual family desserts and special occasions

The Building Blocks of Flavor

Yellow Cake Mix: A convenient shortcut that still yields homemade taste. Choose a quality brand for best results.

Butter: Divided between the caramel base and the cake batter, giving richness throughout. Unsalted works best, but salted is fine too.

Brown Sugar: Creates that signature caramelized topping. Dark brown sugar gives a deeper molasses flavor if you prefer.

Eggs: Provides structure to the cake. Room temperature eggs incorporate more easily.

Crushed Pineapple: The secret to an extra-moist cake. Don’t drain—the juice adds flavor and moisture.

Pineapple Rings: The visual star of the show. Fresh pineapple rings can be substituted but canned ensures consistent thickness.

Maraschino Cherries: Adds that pop of color and nostalgic flavor. Natural maraschino cherries without artificial dyes are available at specialty stores.

Make It Your Own

The Tropical Twist

Add 1/2 cup toasted coconut flakes to the batter and sprinkle some on top after flipping for a tropical variation that pairs beautifully with the pineapple.

Spiced Island Version

Add a teaspoon of cinnamon and 1/2 teaspoon of nutmeg to the batter, then serve with a dollop of rum-spiked whipped cream for a warm-spiced interpretation.

Mini Individual Cakes

Use a muffin tin with a single pineapple ring at the bottom of each cup for individual servings—perfect for potlucks or when portion control matters.

From Batter to Beautiful

Step 1: Prepare Your Canvas

Melt half the butter in your cake pan, spreading it evenly across the bottom and sides. This creates the base for your caramel topping and ensures easy release later. Sprinkle brown sugar evenly over the butter, creating the foundation for that sticky-sweet glaze.

Step 2: Create the Signature Design

Arrange pineapple rings in a single layer on the bottom of the pan. This is your chance to get creative—I sometimes overlap them slightly for more fruit in every bite. Place cherries in the center of each ring and in any empty spaces between rings.

Step 3: Mix the Magic

Combine the cake mix, eggs, crushed pineapple with its juice, and remaining melted butter. The crushed pineapple disappears into the batter, infusing every bite with tropical flavor. Beat until well combined but don’t overmix.

Step 4: Bake and Flip

Pour the batter carefully over your arranged fruit. During baking, the butter and sugar transform into a caramel that soaks into the fruit. After cooling slightly, flip the cake onto a serving plate for that wonderful “ta-da” moment.

Baking Wisdom Worth Sharing

• A cast iron skillet works beautifully for this cake and creates even better caramelization
• If your cake sticks when flipping, run a knife around the edge and gently tap the bottom of the pan
• Let the cake cool exactly 15 minutes—too hot and it falls apart, too cool and the caramel sets too firmly
• For cleaner slices, use a knife dipped in hot water before each cut
• Place a sheet pan under your cake pan during baking to catch any potential caramel overflow
• Don’t substitute oil for the butter in the topping—the butter is essential for proper caramelization

Serving Suggestions

This cake is delightful on its own but truly shines when served slightly warm with a scoop of vanilla ice cream melting into the caramel topping. For a special brunch, pair slices with cups of Kona coffee. If serving as a dessert course, a small glass of dessert wine or aged rum complements the caramelized flavors beautifully.

Storage & Make-Ahead Tips

This cake actually improves overnight as the flavors meld, though the caramel topping softens a bit. Store at room temperature, covered with a cake dome or inverted bowl, for up to 2 days. For longer storage, refrigerate for up to 5 days.

To revive refrigerated cake, warm individual slices in the microwave for 15-20 seconds. I don’t recommend freezing this cake as the texture of the fruit changes upon thawing.

Common Questions Answered

Can I use fresh pineapple instead of canned?

Absolutely! Just be sure to slice it evenly about 1/4-inch thick. You may want to sprinkle a bit more brown sugar on fresh pineapple as it’s typically less sweet than canned.

My cake is too moist in the center. What happened?

Crushed pineapple adds significant moisture. If your cake is consistently too wet, try draining about 1/4 of the pineapple juice before adding to the batter, or extend baking time by 5-8 minutes.

Can I make this recipe gluten-free?

Yes, simply substitute a gluten-free yellow cake mix. The rest of the ingredients are naturally gluten-free.

How do I know exactly when to flip the cake?

The 15-minute cooling time is crucial. Set a timer after removing from the oven. The cake should still be warm but not hot enough to fall apart when inverted.

A Sweet Finale

There’s something magical about pineapple upside down cake—perhaps it’s the retro charm or the dramatic reveal when you flip it over. Whatever draws you to this recipe, it delivers on both nostalgia and flavor. It’s the kind of dessert that doesn’t need fancy techniques or specialty ingredients to impress, just a little patience and the willingness to trust the flip.

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