If you’re ready to turn a classic dessert upside down—in the most delicious way—let me introduce you to Pineapple Right Side Up Cheesecake. This eye-catching treat combines the caramelized, sunny flavors of a pineapple upside-down cake with the creamy, dreamy texture of cheesecake. Picture golden pineapple rings and rich brown sugar on a buttery graham crust, topped with a velvety, pineapple-infused cheesecake layer. Every bite is tropical, tangy, and utterly irresistible, with a perfect balance of flavors and textures that will have everyone swooning for seconds.

Pineapple Right Side Up Cheesecake Recipe - Recipe Image

Ingredients You’ll Need

It’s amazing how a handful of well-chosen ingredients can create something truly spectacular. Each element in this Pineapple Right Side Up Cheesecake brings a unique burst of flavor, richness, or texture that makes the finished dessert unforgettable.

Graham cracker crumbs: The base of your crust, these provide a sweet, sandy crunch that pairs perfectly with creamy cheesecake.
Granulated sugar: Sweetens both crust and filling, enhancing every layer’s flavor.
Unsalted butter: Adds richness and helps bind both the crust and pineapple topping.
Brown sugar: For that classic caramelized pineapple flavor on top.
Pineapple rings (fresh or canned): The star of the show, bringing color, juiciness, and tropical sweetness.
Maraschino cherries (optional): A fun, nostalgic pop of color and flavor, just like the original cake.
Cream cheese: The creamy heart of the cheesecake, so be sure it’s softened for easy mixing.
Vanilla extract: Adds a subtle warmth and depth to the filling.
Eggs: Help set the cheesecake and give it structure.
Sour cream: For tanginess and extra silky smoothness in the filling.
Crushed pineapple, well-drained: Gives the filling a burst of pineapple flavor and keeps things moist without being watery.

How to Make Pineapple Right Side Up Cheesecake

Step 1: Prep Your Pan and Oven

Start by preheating your oven to 325°F (160°C) and lightly greasing a 9-inch springform pan. This ensures your cheesecake releases easily later and bakes evenly. A springform pan is key, making serving and presentation a breeze!

Step 2: Build the Graham Cracker Crust

Mix the graham cracker crumbs, granulated sugar, and melted butter in a bowl until the mixture is like wet sand. Press it firmly and evenly into the bottom of your pan. Bake the crust for 8 to 10 minutes—this quick bake helps the crust hold together and adds a toasty, rich flavor. Let it cool while you prepare the next layer.

Step 3: Caramelize the Pineapple Topping

Melt the butter in a small saucepan, stir in the brown sugar, and cook until bubbling and smooth for about 2 minutes. Pour this golden caramel over your cooled crust. Gently arrange the pineapple rings on top, nestling a maraschino cherry in the center of each if you like. This layer not only looks stunning, but infuses the whole cheesecake with juicy, tropical notes.

Step 4: Make the Creamy Cheesecake Filling

In a large bowl, beat the softened cream cheese until completely smooth—no lumps! Add in the sugar and vanilla extract, mixing until just combined. Beat in the eggs one at a time, scraping the bowl as needed. Next, blend in the sour cream, then gently fold in the well-drained crushed pineapple. Pour this luscious mixture over the pineapple layer and smooth out the top.

Step 5: Bake, Cool, and Chill

Bake your Pineapple Right Side Up Cheesecake for 55 to 65 minutes, until the edges are set but the center has a slight jiggle. Turn off the oven, crack the oven door, and let the cheesecake cool inside for an hour. This gentle cooling helps prevent cracks. Once it’s at room temperature, refrigerate for at least 4 hours or overnight—patience brings perfection!

Step 6: Unmold and Serve

Run a knife around the edge of the pan to loosen the cheesecake, then carefully release the springform. The dazzling pineapple rings should gleam on top! Slice with a sharp knife and serve chilled for the ultimate creamy, fruity experience.

How to Serve Pineapple Right Side Up Cheesecake

Garnishes

For a show-stopping finish, consider adding extra maraschino cherries, a sprinkle of toasted coconut, or a drizzle of pineapple syrup over each slice. A dollop of whipped cream on the side never hurts, either, and really makes those tropical flavors sing.

Side Dishes

Serve your Pineapple Right Side Up Cheesecake with a bright fruit salad, or pair it with a scoop of coconut or vanilla ice cream for an extra indulgent dessert experience. A hot cup of coffee or a tropical tea is also the perfect finishing touch.

Creative Ways to Present

Try serving individual slices on vibrant, colorful plates to highlight the dessert’s sunny palette. For special occasions, consider mini cheesecakes in ramekins or muffin tins, each topped with a pineapple ring and cherry. If you’re entertaining, a platter decorated with fresh pineapple leaves adds an extra wow factor!

Make Ahead and Storage

Storing Leftovers

Leftover Pineapple Right Side Up Cheesecake keeps beautifully in the refrigerator. Cover the cheesecake (or individual slices) tightly with plastic wrap or foil, and it will stay fresh for up to 5 days. The flavors actually deepen as it sits, making each day’s slice even more delicious.

Freezing

To freeze, wrap slices or the whole cheesecake tightly in plastic wrap, then a layer of foil. Store in a freezer-safe container for up to 2 months. Thaw overnight in the refrigerator for best texture—your cheesecake will taste just as dreamy as the day you made it.

Reheating

Cheesecake is best enjoyed chilled, but if you prefer a slightly warmer bite, let a slice sit at room temperature for 20 to 30 minutes before serving. Avoid microwaving, as it can alter the creamy texture and melt the topping.

FAQs

Can I use fresh pineapple instead of canned?

Absolutely! Fresh pineapple gives a wonderful tang and brightness. Just be sure to slice it thin and pat it dry to avoid extra moisture, which can affect the texture of your Pineapple Right Side Up Cheesecake.

How do I prevent cracks in my cheesecake?

Letting the cheesecake cool slowly in the oven with the door cracked is key. Avoid overbeating the eggs and always use room-temperature ingredients for a smooth, crack-free finish.

What’s the best way to slice cheesecake cleanly?

Use a sharp, thin knife dipped in hot water for each cut. Wipe the blade clean between slices for those perfect, picture-worthy pieces of Pineapple Right Side Up Cheesecake.

Can I make this recipe gluten-free?

Yes! Simply substitute gluten-free graham crackers in the crust. All the other ingredients in Pineapple Right Side Up Cheesecake are naturally gluten-free, so it’s an easy swap.

Why does my cheesecake seem too soft after chilling?

If the cheesecake is too soft, it may need a bit more chilling time. Also, make sure the crushed pineapple is very well-drained, as extra moisture can prevent the filling from setting firmly.

Final Thoughts

If you’ve been searching for a dessert that’s as joyful to look at as it is to eat, Pineapple Right Side Up Cheesecake is sure to become your new favorite. It’s a tropical twist on tradition that’s impossible to resist. Give it a try and share it with friends or family—you’ll be the talk of every gathering!

Pineapple Right Side Up Cheesecake Recipe

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4.9 from 19 reviews

Author: admin
Total Time: 1 hour 25 minutes (plus chilling time)
Yield: 10 servings 1x
Diet: Non-Vegetarian

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Description

This Pineapple Right Side Up Cheesecake combines a buttery graham cracker crust with a luscious pineapple topping and a creamy, smooth cheesecake filling. It features a delightful tropical flavor with fresh or canned pineapple rings and maraschino cherries for a classic, eye-catching presentation. Perfect for dessert lovers looking for a fruity twist on traditional cheesecake.

Ingredients

Scale

For the crust:

1½ cups graham cracker crumbs
¼ cup granulated sugar
6 tablespoons unsalted butter, melted

For the pineapple topping:

¼ cup unsalted butter
½ cup brown sugar
6–8 pineapple rings (fresh or canned)
Maraschino cherries (optional)

For the cheesecake filling:

3 (8 oz) packages cream cheese, softened
1 cup granulated sugar
1 teaspoon vanilla extract
3 large eggs
½ cup sour cream
½ cup crushed pineapple, well-drained

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Instructions

Preheat and Prepare Pan: Preheat the oven to 325°F (160°C). Lightly grease a 9-inch springform pan to ensure easy removal of the cheesecake after baking.
Make the crust: In a bowl, combine graham cracker crumbs, granulated sugar, and melted butter. Mix thoroughly until well combined. Press the mixture firmly into the bottom of the prepared springform pan to form an even crust layer. Bake in the preheated oven for 8–10 minutes until set. Remove and allow to cool completely.
Prepare the pineapple topping: In a small saucepan, melt butter over medium heat. Stir in brown sugar and cook, stirring frequently, until the mixture is smooth and bubbling, about 2 minutes. Pour this caramel-like sauce evenly over the cooled crust in the springform pan. Arrange the pineapple rings on top of the sauce in a single layer. If desired, place a maraschino cherry in the center of each pineapple ring for added color and sweetness.
Make the cheesecake filling: In a large mixing bowl, beat the softened cream cheese with an electric mixer until smooth and creamy. Add granulated sugar and vanilla extract, and mix well to combine. Beat in the eggs one at a time, mixing just until incorporated after each addition to prevent overmixing. Fold in the sour cream gently until blended, then carefully fold in the well-drained crushed pineapple to maintain a light texture. Pour the completed filling evenly over the pineapple and crust layers in the pan, smoothing the top with a spatula.
Bake the cheesecake: Place the springform pan in the oven and bake for 55–65 minutes, or until the center is set but still slightly jiggly when shaken gently. Turn off the oven and crack the oven door open; let the cheesecake cool inside the oven for 1 hour to prevent cracking.
Chill the cheesecake: After cooling in the oven, remove the cheesecake and refrigerate it for at least 4 hours, preferably overnight, to allow it to fully set and develop flavor.
Serve: Run a thin knife around the edge of the cheesecake to loosen it from the pan. Carefully remove the sides of the springform pan. Slice the cheesecake into 10 servings and serve chilled for the best texture and taste.

Notes

Ensure the crushed pineapple is well-drained to avoid excess moisture that can affect the texture of the cheesecake filling.
For a bolder pineapple flavor, consider adding a few drops of pineapple extract or increasing the crushed pineapple while slightly reducing the amount of sour cream.
Use room temperature cream cheese and eggs to ensure a smooth batter free of lumps.
Do not overmix the batter once eggs are added to prevent a dense texture.
Allowing the cheesecake to cool gradually in the oven helps prevent cracks on the surface.
Chilling the cheesecake overnight enhances the flavor and makes slicing easier.

Prep Time: 25 minutes
Cook Time: 1 hour
Category: Dessert
Method: Baking
Cuisine: American