Pineapple Upside-Down Cheesecake Recipe

If you think you know cheesecake, just wait until you try this Pineapple Upside-Down Cheesecake! This dreamy dessert gives you the best of two worlds: rich, creamy cheesecake with a glistening crown of caramelized pineapple rings and cherries, all cozied up on a crunchy graham cracker crust. Every bite combines sweet-tart fruit, a hint of vanilla, and the unmistakable tang of classic cheesecake. It’s a showstopper at any dinner table and truly a conversation starter, whether you’re hosting a tropical-inspired brunch or looking for an unforgettable weekend treat.

this Recipe

Ingredients You’ll Need

The magic of Pineapple Upside-Down Cheesecake is how each simple ingredient transforms into a slice of pure nostalgia. Here’s what you’ll need, with a little insight into why each one is so important for taste and texture.

• Unsalted butter (¼ cup, melted): Adds richness and helps that irresistible caramelized layer come to life.
• Brown sugar (½ cup, packed): Essential for that toasty, caramel-like sweetness on the pineapple layer.
• Pineapple rings (6, canned or fresh): The sunny, tangy stars of the topping; fresh or canned both work beautifully.
• Maraschino cherries (6): Tucked into each pineapple ring for a nostalgic, colorful touch and a pop of sweetness.
• Cream cheese (2 x 8-ounce packages, softened): The creamy, dreamy foundation of any good cheesecake.
• Granulated sugar (¾ cup): Balances the tang of the cream cheese with just the right amount of sweetness.
• Large eggs (2): Help bind everything together into a smooth, custardy filling.
• Vanilla extract (1 teaspoon): Adds warmth and rounds out all the flavors.
• Sour cream (½ cup): Lends a gentle tang that makes the filling silky and not too sweet.
• Crushed pineapple (¼ cup, drained): Dotted through the cheesecake for extra bursts of tropical flavor.
• All-purpose flour (1 tablespoon): Just a dab helps the cheesecake set up perfectly.
• Graham cracker crust (1 pre-made 9-inch, or homemade): Buttery and crunchy, the perfect base for all that juicy fruit and creamy filling.

How to Make Pineapple Upside-Down Cheesecake

Step 1: Prepare the Pan and Fruit Layer

Start by preheating your oven to 325°F (160°C). Lightly grease a 9-inch springform pan (this makes releasing the cheesecake later a breeze). Pour in your melted butter and evenly sprinkle the brown sugar over the bottom—your future caramel layer! Arrange the pineapple rings on top of the sugar, then tuck a maraschino cherry into the center of each ring. This set-up gives you that classic, glossy finish when you flip the cheesecake later.

Step 2: Make the Cheesecake Filling

In a large bowl, beat together the softened cream cheese and granulated sugar until the mixture is ultra smooth and fluffy—this is key to a silky filling! Add the eggs, one at a time, mixing well after each addition to keep things light. Stir in the vanilla extract, sour cream, drained crushed pineapple, and flour. Mix everything until just combined, being gentle so your filling stays luscious and creamy.

Step 3: Assemble and Bake

Gently pour the filling over your beautifully arranged pineapple and cherry layer, making sure not to disturb it. Smooth the top lightly. Pop the pan into your preheated oven and bake for 55–65 minutes. You’re looking for the center to be just set and the top to turn ever so slightly golden. The wonderful aroma filling your kitchen is pure anticipation!

Step 4: Cool and Chill

Once the cheesecake is done, allow it to cool to room temperature in the pan—patience is key here to prevent cracks. After that, refrigerate it for at least 4 hours, though overnight is best. This chilling time lets all the flavors meld and the texture set up perfectly.

Step 5: Unmold and Flip

Right before serving, run a knife around the edge to loosen the cake. Release the springform, then set a serving plate on top and invert it. Carefully lift off the pan and reveal that stunning Pineapple Upside-Down Cheesecake top! It’s a moment of pure dessert magic.

How to Serve Pineapple Upside-Down Cheesecake

Garnishes

This showy dessert is already beautiful, but a cloud of freshly whipped cream or a sprinkle of toasted coconut takes it to the next level. A drizzle of pineapple syrup or even a few extra maraschino cherries dotted around the plate makes for an irresistible presentation.

Side Dishes

To make it a truly memorable dessert course, pair your Pineapple Upside-Down Cheesecake with a crisp fruit salad, a scoop of coconut ice cream, or a mug of strong coffee. Each brings out different facets of the cheesecake’s tropical, creamy notes and keeps things balanced after a big meal.

Creative Ways to Present

Why not get playful? Try cutting the cheesecake into mini wedges and serving them in cupcake liners for an easy party treat, or layering cubes of cheesecake with whipped cream and extra fruit in parfait glasses for a stunning, deconstructed look. Sometimes, small details make the experience unforgettable!

Make Ahead and Storage

Storing Leftovers

Leftover Pineapple Upside-Down Cheesecake keeps wonderfully in the fridge. Just store slices in an airtight container, separating layers with parchment paper if you’re stacking them, and enjoy within 4–5 days for the best texture and freshness.

Freezing

This cheesecake freezes surprisingly well! Wrap individual slices or the whole cake (well-chilled) tightly in plastic wrap, followed by a layer of foil. It’ll keep for up to 2 months. Thaw overnight in the fridge before serving for a taste that’s just as luscious as day one.

Reheating

While there’s no need to reheat Pineapple Upside-Down Cheesecake, you can take the chill off by letting slices sit at room temperature for about 20 minutes before serving. This brings out the full creaminess and brightens up the pineapple flavors.

FAQs

Can I make Pineapple Upside-Down Cheesecake in advance?

Absolutely! In fact, chilling overnight is recommended for perfect flavor and clean slices. You can prepare the cheesecake up to two days in advance, keeping it covered in the fridge until you’re ready to invert and serve.

What’s the best way to ensure a clean flip?

The secret is to thoroughly chill the cheesecake and carefully run a knife around the edge before inverting. Placing a serving plate firmly over the pan before flipping helps, and a steady hand never hurts!

Can I use fresh pineapple instead of canned?

Yes, you can absolutely swap in fresh pineapple rings. Just make sure to slice them evenly and pat them dry to prevent sogginess. The fresh fruit gives a slightly brighter, juicier finish to your Pineapple Upside-Down Cheesecake.

Why is my cheesecake cracking on top?

Cheesecake cracks are usually caused by overbaking or rapid temperature changes. To minimize cracking, avoid over-mixing and don’t open the oven door during baking. Resting and chilling the cake slowly helps keep it picture-perfect.

Can I use another crust besides graham cracker?

Definitely! Try a vanilla wafer crust or even a shortbread crust for a delicious twist. Just make sure your crust of choice is sturdy enough to hold all the delightful toppings and filling.

Final Thoughts

This Pineapple Upside-Down Cheesecake is guaranteed to steal the spotlight at any gathering or family dinner. Every slice is a gorgeous blend of caramelized fruit and creamy cheesecake with a tropical twist. I can’t wait for you to give it a try and watch your guests savor every sunny, irresistible bite!

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