Name: Pineapple Upside Down Cheesecake Recipe
Prep time: 20 min
Cook time: 1 h 35 min
Total time: 7 h 40 min
Cuisine: American
Ingredients: 16 ounces cream cheese room temp; 1/2 cup granulated sugar; 2 large eggs; 1/2 cup sour cream; 2 tablespoons pineapple juice; 1 teaspoon vanilla extract; 1/2 cup unsalted butter melted; 1 cup packed light brown sugar; 14 slices canned or fresh pineapple rings; 14 maraschino cherries; 1 1/2 cup + 3 tablespoons all-purpose flour sifted; 1/2 teaspoon baking powder; 1/4 teaspoon baking soda; 1/2 teaspoon salt; 1/2 cup unsalted butter melted; 3/4 cup light brown sugar packed; 1/4 cup granulated sugar; 1 large egg; 1/4 cup sour cream; 1/2 cup milk; 1/4 cup pineapple juice; 1 tablespoon vanilla extract

Jump to Recipe· 4.5 from 39 reviews

If you’re a fan of both cheesecake and classic pineapple upside-down cake, you’re in for a serious treat. This Pineapple Upside Down Cheesecake Recipe is like a flavor party where creamy meets caramelized fruit topped with moist cake—and I promise it’s fan-freaking-tastic. It’s got that nostalgia factor combined with a silky-smooth texture you don’t always find in dessert combos. Stick with me, and I’ll walk you through every step so you nail it perfectly in your own kitchen.

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Why This Recipe Works

Layered Flavor Harmony: The combination of tangy pineapple, buttery caramel, and creamy cheesecake balances beautifully in every bite.
Moist Cake Base: The buttery pineapple upside-down cake on top of the cheesecake gives a tender texture that’s light but rich.
Water Bath Baking: A gentle water bath ensures the cheesecake is silky, crack-free, and perfectly set.
Visual Appeal: The vibrant pineapple rings and maraschino cherries create a stunning and inviting dessert.

Pineapple Upside Down Cheesecake, pineapple cheesecake recipes, upside down cake with cheesecake, caramel pineapple dessert, fruit-topped cheesecake - A two-layer round cake sits on a white marbled surface, with the bottom layer being a light brown sponge cake and the middle layer a thick, smooth cream that is pale yellow. The top layer is another light brown sponge with seven yellow pineapple rings evenly placed on it, each pineapple ring holding a small bright red cherry in the center. The cake looks moist and slightly shiny on top from the pineapple, and the overall shape is round and neatly stacked. In the background, there is a softly blurred aqua blue cloth, a white milk jug, and some out-of-focus flowers in soft pink and orange colors. Photo taken with an iphone --ar 2:3 --v 7

Ingredients & Why They Work

This recipe brings together ingredients that each have a special job to do, creating a texture and flavor combo that truly shines. From cream cheese that makes the filling luxuriously smooth to the pineapple juice and brown sugar that give deep caramel notes, every ingredient plays its part. Plus, there’s a method to how you select them, so I’ve added a few tips to help you pick the best.

Cream Cheese: Room temperature for a smooth soufflé-like texture; cold cream cheese can make your batter lumpy.
Granulated Sugar & Brown Sugar: Brown sugar adds that luscious caramel flavor, while granulated sugar keeps sweetness balanced.
Eggs: Bind the cheesecake filling gently – add them one at a time for better mixing and to avoid overworking the batter.
Sour Cream: Adds tang and moisture, keeping the cheesecake rich yet vibrant without dryness.
Pineapple Juice: Infuses tropical brightness straight into the cheesecake batter and cake.
Unsalted Butter: Melted butter enriches the cake and topping, giving buttery depth that pairs well with caramelized sugar.
Flour (All-purpose): Sifted for lightness and even mixing, essential for the cake layers.
Baking Powder & Soda: Create lift and a nice crumb that complements creamy cheesecake.
Vanilla Extract: Enhances overall flavor with subtle warmth and sweetness.
Pineapple Rings & Maraschino Cherries: Classic decoration that doubles as natural sweet accents—opt for fresh pineapple if possible for extra vibrancy.

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Note: You’ll find the complete list of ingredients, along with their exact measurements, in the printable recipe card at the bottom of this post.

Tweak to Your Taste

I like to customize this Pineapple Upside Down Cheesecake Recipe depending on the occasion. Sometimes, I swap the maraschino cherries with fresh raspberries for a tart twist. Other times, I sneak in a pinch of cinnamon or nutmeg into the cake batter to add cozy warmth—especially during cooler months.

Variation: For a dairy-free version, try using a vegan cream cheese and coconut milk. It’s surprisingly delicious and just as creamy.
Add-Ins: Chopped toasted pecans in the cake batter add a lovely crunch contrast.
Sweetness Level: If you prefer less sweetness, reduce the granulated sugar in the cake batter by 1/8 cup and taste as you go.

Step-by-Step: How I Make Pineapple Upside Down Cheesecake Recipe

Step 1: Prep and Baking the Cheesecake Base

First things first: preheat your oven to 325°F and grease a 9-inch springform pan. Wrap the bottom and sides well with heavy-duty foil to prevent leaks during the water bath.

I find whipping the cream cheese with granulated sugar until super smooth is key—use an electric mixer and don’t rush this part to avoid lumps. Then, beat in the eggs one at a time, scraping the bowl as you go to keep everything blended evenly. Adding sour cream, pineapple juice, and vanilla last gives that signature brightness and silkiness. Pour this batter into the prepared pan, place it into a larger roasting pan, and carefully fill that with hot water halfway up the sides. This gentle cooking keeps the cheesecake creamy and crack-free.

Bake it at 300°F for 45 minutes, then turn off the oven and leave the cheesecake inside for another 20 minutes to set perfectly. Once it’s out, let it cool completely, then pop it in the fridge overnight. Trust me, that patience pays off big time!

Step 2: Creating the Pineapple Upside-Down Cake Topping

While the cheesecake chills, melt butter and divide it evenly between two 9-inch cake pans. Sprinkle brown sugar on top, then arrange your pineapple rings and maraschino cherries beautifully. This topping is what makes the cake pop visually and flavor-wise—don’t rush arranging those fruit slices! I usually start from the center and work my way out for a neat look.

Step 3: Mixing and Baking the Cake Layers

Next, whisk together the sifted flour, baking powder, baking soda, and salt in a large bowl. In another bowl, mix melted butter with both sugars until smooth, then whisk in egg, sour cream, milk, pineapple juice, and vanilla. Combine the wet and dry ingredients just until no lumps remain—as overmixing can make the cake dense.

Divide the batter evenly between the two cake pans, spreading gently over your arranged pineapple rings and cherries. Bake at 350°F for 25–30 minutes until golden and a toothpick inserted near the center comes out clean.

Cool your cakes in their pans for about 10 minutes before flipping them out onto a cooling rack. This brief rest helps keep the fruit topping in place.

Step 4: Assembling Your Pineapple Upside Down Cheesecake

Now for the fun part! Carefully remove the springform ring from your cheesecake and gently lift it off the bottom (an offset spatula is a helpful tool here). Place the cheesecake on top of one of your cake layers, then stack the second cake layer on top. If you want, chill the whole cake before serving to let the layers meld.

I usually add a few dollops of whipped cream right before serving for that extra creamy contrast. It’s a showstopper every time.

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Pro Tips for Making Pineapple Upside Down Cheesecake Recipe

Room Temperature Ingredients: Always bring cream cheese, eggs, and sour cream to room temp before mixing to avoid a lumpy batter.
Use a Water Bath: Baking the cheesecake in a water bath keeps it creamy and prevents the dreaded cracks.
Don’t Overmix Cake Batter: Stir just until combined to maintain a tender crumb—you want fluffiness, not toughness.
Invert with Care: Gently flip the cake pans to keep the pineapple and cherries perfectly arranged and undisturbed.

How to Serve Pineapple Upside Down Cheesecake Recipe

Garnishes

I love keeping it simple with a few swirls of lightly sweetened whipped cream and a sprinkle of toasted coconut flakes for texture. Sometimes I toss fresh mint leaves for a fresh contrast to the rich cheesecake layers. These finishing touches make the presentation pop without overpowering the natural tropical flavors.

Side Dishes

This dessert shines on its own but pairs nicely with a scoop of vanilla bean ice cream or a simple raspberry coulis on the side if you want a bit of tartness to balance the sweetness. For drinks, I find a chilled glass of pineapple or mango juice complements it perfectly.

Creative Ways to Present

For a festive touch, I once layered mini versions in clear parfait glasses, alternating bite-sized cake pieces, cheesecake layers, pineapple chunks, and a cherry on top—instagram worthy! You can also dust with powdered sugar or drizzle a little caramel for a cozy, homey vibe on special occasions.

Make Ahead and Storage

Storing Leftovers

Once assembled, cover the cheesecake tightly with plastic wrap or store in an airtight container and keep it in the fridge—it stays fresh and moist for up to 4 days. I like to slice it before storing because it reheats nicely, too.

Freezing

You can freeze individual slices wrapped in plastic wrap and foil for up to 2 months. Just thaw overnight in the fridge before serving. The texture remains surprisingly good, though I’d skip the whipped cream garnish if freezing ahead.

Reheating

For a warmed slice, pop it in the microwave on medium-low power for about 20 seconds—just enough to take the chill off without melting the cheesecake. Serve immediately, maybe with a fresh dollop of whipped cream to revive that luscious mouthfeel.

FAQs

Can I use fresh pineapple instead of canned for this Pineapple Upside Down Cheesecake Recipe?

Absolutely! Fresh pineapple adds a natural brightness and less syrupy sweetness than canned. Just make sure to slice rings evenly and pat them dry to prevent excess moisture from affecting the caramel topping.
Why do I need to use a water bath when baking the cheesecake?

The water bath creates gentle, even heat around the cheesecake, preventing cracks and keeping the texture silky rather than dry or crumbly. It’s a simple trick that makes a big difference in your final dessert.
Can I make the cake layers and cheesecake ahead of time?

Yes! You can bake the cheesecake and cakes a day or two in advance. Just store them separately in the fridge and assemble on the day you want to serve. This spreads out the work and helps each component chill properly for best results.
What’s the best way to avoid overmixing the batter?

Mix just until you no longer see flour streaks. Stop as soon as the batter looks uniform, as overmixing develops gluten which can make the cake dense and tough. Using a spatula for the final folds helps keep it light.

Final Thoughts

This Pineapple Upside Down Cheesecake Recipe holds a special place in my recipe box because it combines two classic favorites with a fresh twist that always gets compliments. The creamy, tangy cheesecake with the caramelized pineapple topping is a match made in dessert heaven, and once you try it, you’ll want to make it again and again. So grab your mixer and pineapple rings—you’re about to create a show-stopping treat that your friends and family will be raving about!