Get ready to wow your guests, your family, or just treat yourself to an unforgettable dessert: Pineapple Upside Down Cheesecake Cake. This showstopper combines the caramelized, fruity magic of a classic pineapple upside down cake with the dreamy, creamy decadence of a New York-style cheesecake, all in one gorgeous layered masterpiece. It’s a celebration of texture and flavor: juicy pineapples, rich vanilla cheesecake, and a buttery, golden cake come together for a slice of pure happiness. Whether you’re baking for a special occasion or just because, this Pineapple Upside Down Cheesecake Cake is destined to become your new signature dessert.

Pineapple Upside Down Cheesecake Cake Recipe - Recipe Image

Ingredients You’ll Need

Every component of this Pineapple Upside Down Cheesecake Cake has a starring role, and the ingredients list is surprisingly straightforward. Each piece—from the sweet pineapple rings to the luscious cream cheese—plays a part in creating a dessert that is both familiar and spectacular.

Graham cracker crumbs: For a golden, crumbly crust that anchors the cheesecake layer with a touch of nostalgia.
Sugar: Both the crust and filling rely on sugar for sweetness and caramelization—don’t skimp on this staple!
Melted butter: Adds richness and holds the crust together while lending buttery goodness throughout the cake.
Cream cheese (Philadelphia recommended): The backbone of a creamy, smooth cheesecake; room temperature makes for the silkiest texture.
Cornstarch: Gives the cheesecake its signature, velvety stability.
Vanilla extract: Enhances every layer with fragrant warmth.
Extra large eggs: Essential for structure and richness in both cheesecake and cake layers—room temperature gives the best results.
Heavy cream: For a light, billowy, ultra-creamy cheesecake texture.
Pineapple slices in juice (canned): The star fruit adds bright, tropical flavor and beautiful golden rings.
Brown sugar: Melts into the iconic pineapple topping, creating a gooey, caramelized surface.
Salted butter: Used in both cake and topping; brings out all the other flavors.
Maraschino cherries: For pops of color and classic upside down cake vibes.
Buttermilk: Ensures the cake layer is ultra-tender with a slight tang.
Baking powder & baking soda: Lift the cake to airy perfection.
Salt: Just a touch unlocks all the sweet and tangy flavors.
All purpose flour: Forms the tender, sturdy cake that holds up to all that juicy fruit.
Extra cherries & warmed caramel sauce: Perfect for finishing each slice in pure dessert bliss.

How to Make Pineapple Upside Down Cheesecake Cake

Step 1: Prepare and Bake the Cheesecake

Start your Pineapple Upside Down Cheesecake Cake adventure the day before you plan to serve it—this gives your cheesecake time to set up and build those unforgettable creamy layers. Wrap your 9-inch springform pan’s bottom and sides tightly with heavy-duty foil; this step is essential for leak-proof water bath baking. Blend graham cracker crumbs, sugar, and melted butter, pressing this mixture firmly onto the base (and a bit up the sides if you like). After a brief bake, let the crust cool while you mix up your filling: beat softened cream cheese, sugar, cornstarch, and vanilla until creamy, adding eggs one at a time, then fold in heavy cream. Pour the cheesecake mixture into the cooled crust, nestle the pan in a hot water bath, and bake until just set with a delicate jiggle—about 1 hour and 15 minutes. Cool completely, loosely cover, and chill overnight in the fridge for the perfect texture.

Step 2: Make the Pineapple Upside Down Cake Layer

The next day, preheat your oven and prepare a 9-inch cake pan with a slick of cooking spray. Gently melt brown sugar and butter in a saucepan until combined into a caramel sauce, then pour it straight into your cake pan, swirling to cover the bottom evenly. Lay out your dry pineapple slices and maraschino cherries in whatever design makes you smile—this will be the gorgeous, gooey top once flipped! Whisk together the cake batter: melted butter, sugar, eggs, buttermilk, vanilla, and dry ingredients, stirring just until smooth. Carefully pour the batter over the fruit, anchoring everything together.

Step 3: Bake and Invert the Cake

Slide your assembled pan into a 350-degree oven and bake for about 30 minutes, until a toothpick comes out clean. For the big reveal, let the cake cool for just a minute, then confidently invert it onto a flat baking sheet or platter so the caramelized pineapple and cherries are on top. Let it cool completely—you’re building the perfect foundation for that dreamy cheesecake crown.

Step 4: Assemble the Pineapple Upside Down Cheesecake Cake

It’s time for the dessert equivalent of a high-five! Gently remove your cheesecake from the fridge, and release the sides from the springform pan, keeping it on the base for stability. Place the cheesecake on your serving platter. Using a large spatula or a cake lifter, carefully slide your fully cooled upside down cake off the pan and position it on top of the cheesecake layer. The result? A sky-high, jaw-dropping Pineapple Upside Down Cheesecake Cake guaranteed to turn heads and inspire second helpings.

Step 5: Slice and Serve

With a sharp, clean knife, cut beautiful tall slices and drizzle with extra warm caramel sauce. Adorn with more maraschino cherries if you’re feeling extra festive, then serve and gather the compliments—you’ve earned them!

How to Serve Pineapple Upside Down Cheesecake Cake

Garnishes

A little extra love goes a long way! Before serving, add a generous drizzle of warm caramel sauce over each slice and top with extra maraschino cherries for color and whimsy. A sprinkle of toasted coconut or a light dusting of powdered sugar can also make this Pineapple Upside Down Cheesecake Cake even more magical.

Side Dishes

Since this cake is the star, keep sides light and refreshing—think a bowl of mixed tropical fruit, a scoop of vanilla bean ice cream, or even a sparkling fruit punch. These pairings help balance the richness and let every bite of your Pineapple Upside Down Cheesecake Cake shine.

Creative Ways to Present

Impress your guests with a dramatic presentation: try slicing the entire cake in advance and fanning the pieces on a platter for easy serving, or set up a DIY dessert bar with bowls of different garnishes for everyone to customize their own slice. For extra fun at parties, cut small cubes of Pineapple Upside Down Cheesecake Cake and serve them as indulgent mini-dessert bites on toothpicks.

Make Ahead and Storage

Storing Leftovers

Pineapple Upside Down Cheesecake Cake stores beautifully in the refrigerator. Simply cover the cake tightly with plastic wrap or transfer slices to an airtight container. It will keep for up to 4 days, and you’ll find the flavors mellow together deliciously as it sits.

Freezing

If you want to make this treat well in advance, you can freeze individual slices or the whole cake (without extra toppings). Wrap well in plastic, then foil, and store in an airtight container for up to 2 months. Thaw overnight in the refrigerator; the texture will remain creamy and just as wow-worthy as day one.

Reheating

For the best experience, let refrigerated or thawed slices sit at room temperature for about 30 minutes before serving. If you prefer, a few seconds in the microwave (just 10–15!) can gently warm up each piece. Gently heat the caramel sauce separately and pour over each slice right before serving.

FAQs

Can I make Pineapple Upside Down Cheesecake Cake in advance?

Absolutely! Both layers can be prepared separately a day ahead. The cheesecake especially benefits from chilling overnight—just assemble everything on the day you plan to serve for maximum freshness and structure.

What’s the best way to avoid cracks in the cheesecake layer?

Using a water bath as directed is your best defense against cracks. Slowly cooling the cheesecake and refrigerating overnight seals in that ultra-smooth texture for your Pineapple Upside Down Cheesecake Cake.

Can I use fresh pineapple instead of canned?

Definitely! Just be sure to slice the fresh pineapple thinly and pat it dry with paper towels—this will help the fruit caramelize beautifully and keep the layers from becoming too moist.

How do I keep the pineapple and cherries from sliding off when flipping?

Pat your fruit dry before arranging it over the butter-brown sugar layer; this prevents slipping. Once the cake is fully baked, invert it while still just warm, and let it cool completely before moving or assembling with the cheesecake.

Is there a way to lighten up this recipe?

For a lighter Pineapple Upside Down Cheesecake Cake, you can use light cream cheese and swap out some of the sugar, but keep in mind that the texture and flavor’s richness are part of what makes this cake so special!

Final Thoughts

If you’re searching for a dessert that’s as fun to make as it is to eat, don’t miss this Pineapple Upside Down Cheesecake Cake. It’s a crowd-pleaser for all ages, bursting with tropical flavor and creamy layers. Give it a try and make some delicious memories—the hardest part will be stopping at just one slice!