Pineapple Upside-Down Cheesecake Recipe

If you love the classic pineapple upside-down cake and the creamy richness of cheesecake, this Pineapple Upside-Down Cheesecake Recipe is going to be your new favorite dessert. It’s got that beautiful caramelized pineapple topping that makes every bite sing, paired with a smooth and luscious cheesecake base. I’ve always found it to be a showstopper for gatherings, whether it’s a summer BBQ or a festive holiday table.

What makes this Pineapple Upside-Down Cheesecake Recipe so special is how the layers come together: the buttery graham cracker crust presses right on top of the pineapple rings and brown sugar glaze, creating this gorgeous, gooey topping once you flip it out of the pan. Trust me, once you try it, you’ll feel like a dessert rockstar every time you serve it.

Ingredients You’ll Need

The beauty of this recipe is in its simplicity and quality ingredients. Each one plays a key role in balancing texture and flavor, so it’s worth grabbing the freshest cream cheese and good pineapple, canned or fresh, to get that perfect caramelized sweetness.

• Graham cracker crumbs: This makes a sturdy and buttery crust. If you want a richer flavor, go for honey graham crackers.
• Unsalted butter: Melting it helps bind the crust and also gives that nice toasted aroma.
• Brown sugar: Essential for that caramelized, deep sweetness under the pineapple rings.
• Pineapple rings: Canned pineapple works best for even caramelization and consistent sweetness, but fresh can be great if you like a bit more tang.
• Maraschino cherries: Classic spots of color and a little burst of sugary fun right in the center of each pineapple ring.
• Cream cheese (softened): The star of the cheesecake filling! Make sure it’s fully softened to avoid lumps.
• Granulated sugar: Balances the tanginess of the cream cheese and pineapple.
• Sour cream: Adds creaminess and a slight tang that keeps the cheesecake from being too sweet.
• Vanilla extract: Just a splash to round out the flavors beautifully.
• Eggs: They give structure to the cheesecake—add them one at a time for a smooth mix.

Variations

One of the things I love about this Pineapple Upside-Down Cheesecake Recipe is how easy it is to make your own. Feel free to swap out ingredients or add a twist — it’s your kitchen, after all!

• Variation: I sometimes add a pinch of cinnamon or nutmeg to the crust for a warm spice undertone, which gives a cozy feeling that’s perfect for colder months.
• Variation: For a tropical booster, try adding shredded coconut to the crust or sprinkling some toasted coconut flakes just before serving.
• Variation: If you want to keep it lighter, swap sour cream for Greek yogurt—it adds tang with fewer calories.
• Variation: For a crowd that’s avoiding dairy, I’ve experimented with vegan cream cheese and coconut cream, and while it’s different, it’s still a sweet seasonal treat.

How to Make Pineapple Upside-Down Cheesecake Recipe

Step 1: Prepare the Pineapple Topping

Start by preheating your oven to 325°F and greasing a springform pan thoroughly. Sprinkle the brown sugar evenly on the bottom—this is the magic that caramelizes during baking. Arrange your pineapple rings over the sugar, making sure they don’t overlap, and pop a maraschino cherry right into the center of each ring. Finally, drizzle the melted butter over the pineapple and sugar so everything gets that beautiful glossy finish as it bakes.

Step 2: Make the Crust and Chill

Mix your graham cracker crumbs with melted butter until all crumbs are evenly moistened—this will make the crust hold together nicely. Press the mixture evenly over the pineapple and brown sugar layer; don’t press too hard or you’ll squish the pineapples out of place. Pop the pan into the freezer for about 10 to 15 minutes to firm up that crust before adding the cheesecake filling. This little step helps keep your layers distinct and clean once baked.

Step 3: Make the Cheesecake Filling

In a large bowl, beat the softened cream cheese and sugar together until smooth and creamy. It’s important to start with room temperature cream cheese to avoid lumps. Add eggs one at a time, mixing just enough to combine before adding the next – this keeps the filling silky and prevents cracks during baking. Stir in sour cream and vanilla extract last, mixing until everything is nicely blended and smooth.

Step 4: Bake in a Water Bath

Pour the cheesecake batter gently over the crust and pineapple topping, smoothing the surface with a spatula. Here’s a pro tip: bake your cheesecake in a water bath to prevent cracking and ensure even cooking. Wrap the outside of your springform pan with foil to avoid leaks, place it in a larger pan filled halfway with hot water, and bake for 60 to 70 minutes. The cheesecake is done when the edges are set but the center still has a slight jiggle.

Step 5: Cool and Chill Overnight

Once out of the oven, turn off the heat and crack the oven door slightly—letting it cool slowly for about an hour helps prevent cracks and keeps the texture perfect. Then, refrigerate your cheesecake for at least 4 hours, but I honestly recommend overnight for the best flavor and firmness. The chilling is crucial to give you that clean slice when you flip it!

Step 6: Flip and Serve

When it’s fully chilled, run a knife gently around the pan’s edge to loosen the cheesecake. Release the springform and place a serving plate on top, then carefully flip the whole pan over so the pineapple topping is on top and the graham cracker crust is the base. This unveiling moment is the best part—those golden rings glistening with cherries always get a whoosh from guests.

How to Serve Pineapple Upside-Down Cheesecake Recipe

Garnishes

I like to keep it simple with this one—the caramelized pineapple and cherries are showstoppers on their own. Sometimes, I sprinkle a few toasted coconut flakes or fresh mint leaves for a pop of color and extra zing. A light dusting of powdered sugar can add a pretty, delicate finish if you’re serving it for a special occasion.

Side Dishes

This cheesecake pairs wonderfully with a scoop of vanilla bean ice cream or a dollop of whipped cream to add creaminess and help balance the caramel sweetness. If it’s summertime, fresh berries alongside the slices brighten things up beautifully.

Creative Ways to Present

For holidays or birthdays, I’ve presented this cheesecake on a decorative wooden board with edible flowers for a tropical, festive touch. You can even serve individual mini upside-down cheesecakes in ramekins for an elegant finger food twist—that always gets rave reviews!

Make Ahead and Storage

Storing Leftovers

Leftover Pineapple Upside-Down Cheesecake keeps perfectly in the fridge for up to 4 days, wrapped tightly with plastic wrap or stored in an airtight container to prevent it from drying out or absorbing fridge odors. I always make sure to slice it nicely so I can grab a piece easily whenever a sweet craving hits.

Freezing

I’ve frozen this cheesecake a couple of times with good results. Slice it into pieces, wrap each tightly with plastic wrap and foil to protect from freezer burn. When you want a slice, thaw in the fridge overnight. The texture holds up well, though I recommend enjoying it within 2 months for best flavor.

Reheating

Cheesecake is best enjoyed chilled, so reheating isn’t usually necessary. However, if you like it a little warmer, take it out of the fridge 20–30 minutes before serving to let it come closer to room temperature—this brings out the flavors without melting it.

FAQs

Final Thoughts

This Pineapple Upside-Down Cheesecake Recipe holds a special place in my kitchen for its perfect balance of textures and flavors. I love how it combines the tropical sweetness of pineapple with the creamy indulgence of cheesecake, making every slice a little celebration. If you’re looking for a dessert that’s both impressive and surprisingly straightforward, I can’t recommend this enough — give it a try and get ready for the compliments!

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