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If you’re looking for a show-stopping dessert that brings together the tropical charm of pineapple and the rich creaminess of cheesecake, then this Pineapple Upside-Down Cheesecake Recipe is exactly what you need. Imagine caramelized pineapple rings and maraschino cherries perfectly arranged beneath a luscious, velvety cheesecake, all sitting atop a buttery graham cracker crust. Each bite bursts with layers of flavor and texture that will have everyone asking for seconds. This dessert elevates a classic upside-down cake by blending it with the indulgence of cheesecake, resulting in something truly unforgettable.

Ingredients You’ll Need
The magic of this dessert lies in its simplicity. Every ingredient plays an essential role in creating the perfect harmony of sweet, tangy, and creamy elements. From the crisp, buttery crust to the rich filling and the caramelized fruit topping, each component is carefully chosen to complement one another beautifully.
- Graham cracker crumbs (1 1/2 cups): Provide a crunchy, flavorful base that holds everything together with just the right amount of sweetness.
- Granulated sugar (1/4 cup + 1 cup): Used both in the crust and filling to balance flavors without overpowering the fruit’s natural tang.
- Melted butter (6 tablespoons + 1/4 cup unsalted): Adds richness and helps achieve that perfect crisp crust and luscious caramel sauce.
- Packed brown sugar (1/2 cup): Essential for creating that deep, caramelized topping that makes this dessert so special.
- Pineapple rings (10–12): Fresh or canned, these are the star attraction that provide juicy bursts of tropical sweetness.
- Maraschino cherries: Placed in the center of each pineapple ring for a pop of color and fun flavor contrast.
- Cream cheese (3 blocks, 8 oz each, softened): The heart of the cheesecake — smooth, creamy, and tangy to perfection.
- Sour cream (1/2 cup): Adds moisture and a subtle tang, making the cheesecake extra creamy and tender.
- Vanilla extract (1 teaspoon): Enhances the sweetness and adds warmth to the cheesecake filling.
- Large eggs (3): Bind the filling ingredients and help achieve that perfect set.
- Crushed pineapple (1/2 cup, drained well): Mixed into the filling to infuse your cheesecake with tropical flavor throughout.
How to Make Pineapple Upside-Down Cheesecake Recipe
Step 1: Prepare the Pineapple Topping
Start by creating the caramel base that gives this dessert its iconic shine and flavor. Melt unsalted butter and packed brown sugar together in a small saucepan over medium heat. Once it starts bubbling and thickening into a rich caramel, pour it evenly into a greased 9-inch springform pan. Carefully arrange the pineapple rings on top of this luscious caramel, and place a maraschino cherry in the center of each ring. Setting this pans the foundation for an amazing presentation and a scrumptious beginning to the dish.
Step 2: Make the Graham Cracker Crust
Next, mix graham cracker crumbs, granulated sugar, and melted butter until the crumbs are evenly coated and hold together when pressed. Gently press this crumbly mixture on top of the pineapple rings, ensuring it covers the rings completely and extends slightly up the pan’s sides. Pop the pan in the fridge while you whip up the cheesecake filling. This chilling step helps the crust firm up and stay crisp through baking.
Step 3: Preheat and Prepare for Baking
Preheating your oven to 325°F (160°C) is key for a slow, gentle bake. To protect your cheesecake from water seeping in during the water bath method, wrap the outside of your springform pan tightly with aluminum foil. Place the wrapped pan inside a larger baking dish—this is where you’ll add hot water later to help your cheesecake bake evenly and stay creamy without cracking.
Step 4: Make the Cheesecake Filling
In a large bowl, beat the softened cream cheese and granulated sugar until completely smooth. Add sour cream and vanilla extract, mixing until well combined. One at a time, beat in the eggs just until incorporated—overmixing can invite cracks. Finally, fold in the well-drained crushed pineapple to distribute that bright, tropical flavor through the creamy filling.
Step 5: Assemble and Bake
Pour your cheesecake filling over the chilled crust, smoothing the top gently. Carefully place the springform pan into the larger baking dish, then pour hot water into the bigger dish until it reaches halfway up the sides of the springform pan. This water bath method is a secret to achieving that silky, crack-free texture we all love. Bake for 60 to 70 minutes, or until the cheesecake’s center is just set but still jiggles slightly when nudged.
Step 6: Cool and Chill
Once baked, remove the cheesecake from the water bath and allow it to come to room temperature on your countertop. After cooling, transfer it to the refrigerator for at least 4 hours—overnight is best. This chilling step not only firms the cheesecake but also lets the flavors meld beautifully.
Step 7: Flip and Serve Your Pineapple Upside-Down Cheesecake Recipe
Carefully run a knife around the edges to loosen your masterpiece, then place a serving platter on top and invert the pan to reveal the caramelized pineapple and cherry topping. Slice, serve, and brace yourself for the well-deserved compliments that are sure to come your way.
How to Serve Pineapple Upside-Down Cheesecake Recipe

Garnishes
Elevate your presentation by adding a few fresh mint leaves on top of the inverted pineapple rings—this splash of green offers a refreshing contrast. A light dusting of powdered sugar or a drizzle of warm caramel sauce can also enhance appearance and flavor, making your cheesecake even more irresistible.
Side Dishes
If you want to serve your Pineapple Upside-Down Cheesecake Recipe alongside something else, consider fresh fruit salad or a coconut sorbet. These options complement the tropical notes of the dessert and keep the overall meal light and balanced.
Creative Ways to Present
Try serving individual mini cheesecakes using muffin tins lined with parchment paper for single servings with the same delightful layers and toppings. Alternatively, make perfect rounds by cutting with a cookie cutter and plating with a dollop of whipped cream and toasted coconut flakes for a festive flair.
Make Ahead and Storage
Storing Leftovers
After enjoying your cheesecake, any leftovers should be tightly wrapped with plastic wrap or stored in an airtight container in the refrigerator. This keeps the dessert fresh and delicious for up to 4 days, maintaining that creamy texture and vibrant flavor.
Freezing
The Pineapple Upside-Down Cheesecake Recipe freezes beautifully. For best results, wrap the cheesecake or individual slices tightly in plastic wrap and then foil before placing in the freezer. It can be stored frozen for up to 2 months without losing its quality.
Reheating
When ready to enjoy frozen cheesecake, thaw it in the refrigerator overnight. Avoid microwaving as it can alter the texture. If you want a warm twist, serve chilled cheesecake with a side of warm caramel sauce or gently warm fruit compote instead.
FAQs
Can I use fresh pineapple instead of canned?
Absolutely! Fresh pineapple offers a wonderfully vibrant flavor and texture. Just make sure to slice rings evenly and drain any excess juice well to avoid a soggy base.
Do I have to use a water bath?
While not mandatory, baking the cheesecake in a water bath significantly improves the texture by providing gentle, even heat that prevents cracking and ensures creaminess.
Can this cheesecake be made gluten-free?
Yes! Substitute the graham cracker crumbs with gluten-free graham crackers or crushed gluten-free cookies for a delicious gluten-free version.
Is it okay to prepare this cheesecake in advance?
Definitely. This cheesecake actually tastes better after resting overnight. Preparing it a day ahead allows the flavors to meld and the texture to set perfectly for serving.
How do I prevent the pineapple from releasing too much juice?
Draining the crushed pineapple thoroughly and using canned pineapple rings that are well-drained help control excess moisture. Also, pressing the crust slightly up the sides prevents sogginess from any juice that might escape.
Final Thoughts
It’s rare to find a dessert that feels both classic and tropical all at once, but this Pineapple Upside-Down Cheesecake Recipe truly nails it. Whether you’re impressing guests or treating yourself, the combination of caramelized pineapple, creamy cheesecake, and buttery crust is a guaranteed crowd-pleaser. So go ahead, give this recipe a try—you might just find your new favorite dessert to savor and share!
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Pineapple Upside-Down Cheesecake Recipe
- Prep Time: 40 minutes
- Cook Time: 1 hour 10 minutes
- Total Time: 5 hours 40 minutes
- Yield: 12 servings
- Category: Dessert
- Method: Baking
- Cuisine: American
Description
A luscious Pineapple Upside-Down Cheesecake combining the classic caramelized pineapple topping with a creamy, smooth cheesecake. This elegant dessert features a graham cracker crust layered over a rich cream cheese filling enhanced with crushed pineapple, baked in a water bath for perfect texture, and flipped to reveal the beautiful pineapple and cherry decoration.
Ingredients
Pineapple Topping
- 1/2 cup packed brown sugar
- 1/4 cup unsalted butter
- 10–12 pineapple rings (canned or fresh)
- Maraschino cherries (one for each ring)
Crust
- 1 1/2 cups graham cracker crumbs
- 1/4 cup granulated sugar
- 6 tablespoons melted butter
Cheesecake Filling
- 3 (8 oz) blocks cream cheese, softened
- 1 cup granulated sugar
- 1/2 cup sour cream
- 1 teaspoon vanilla extract
- 3 large eggs
- 1/2 cup crushed pineapple (drained well)
Instructions
- Prepare the pineapple topping: In a small saucepan, melt the unsalted butter and brown sugar over medium heat until it begins to bubble and forms a caramel sauce. Pour this mixture evenly into the bottom of a greased 9-inch springform pan. Arrange the pineapple rings atop the caramel, and place a maraschino cherry in the center of each ring. Set aside to cool slightly.
- Make the crust: In a mixing bowl, combine the graham cracker crumbs, granulated sugar, and melted butter. Stir until the mixture is fully combined and holds together when pressed. Press this crust mixture over the pineapple rings in the pan, spreading it evenly and pressing slightly up the sides. Chill the crust in the refrigerator while preparing the cheesecake filling.
- Preheat oven and prepare water bath: Preheat your oven to 325°F (160°C). Wrap the outside of the springform pan with aluminum foil tightly to prevent water from leaking in during baking. Place the wrapped pan inside a larger baking dish or roasting pan that can hold hot water.
- Make the cheesecake filling: In a large bowl, beat the softened cream cheese and granulated sugar together until smooth and creamy. Add the sour cream and vanilla extract, mixing until well incorporated. Add the eggs one at a time, beating gently after each addition just until combined—avoid overmixing. Fold in the well-drained crushed pineapple gently to maintain texture.
- Assemble and bake: Pour the cheesecake filling over the prepared crust in the springform pan, spreading it evenly. Place the springform pan inside the larger pan, then pour hot water into the outer pan until it reaches halfway up the sides of the cheesecake pan, creating a water bath to ensure even, gentle baking. Bake for 60 to 70 minutes, or until the center of the cheesecake is just set but still slightly jiggly.
- Cool and chill: Remove the springform pan from the water bath and discard the water. Let the cheesecake cool completely to room temperature on a wire rack. Once cooled, refrigerate for at least 4 hours or overnight to allow the cheesecake to set fully.
- Flip and serve: Run a knife around the edges of the cheesecake to loosen it from the pan. Carefully release the springform pan and invert the cheesecake onto a serving platter so the pineapple rings and cherries are displayed on top. Slice and serve chilled.
Notes
- Use fresh or canned pineapple rings as preferred, but ensure crushed pineapple is well drained to avoid excess moisture in the filling.
- Wrapping the springform pan tightly with aluminum foil is crucial to prevent water from leaking into the cheesecake during the water bath bake.
- Baking in a water bath prevents cracks and ensures a smooth, creamy texture.
- For best flavor and texture, chill the cheesecake overnight before serving.
- You can substitute maraschino cherries with fresh cherries or omit if preferred.
- To warm the caramel topping slightly before assembling the crust helps it spread evenly.

