If you’re ready for a jaw-dropping showstopper dessert with a dreamy tropical twist, you must try Pineapple Upside-Down Cheesecake. This dazzling hybrid brings together the caramel-kissed golden pineapple topping of the classic upside-down cake and the creamy luxury of New York–style cheesecake, all tucked into a buttery graham cracker crust. It’s an explosion of sunny flavors and textures, a recipe that’s surprisingly easy to make and absolutely destined to be the brightest star at any gathering.

Pineapple Upside-Down Cheesecake Recipe - Recipe Image

Ingredients You’ll Need

The magic of this Pineapple Upside-Down Cheesecake comes from a handful of everyday ingredients—each chosen for their essential role in creating layers of flavor, color, and richness. Don’t overlook the details, as every component shines in its own delicious way!

Butter (unsalted): Both in the topping and crust, it gives that unmistakable richness and helps everything hold together beautifully.
Brown sugar: Melts into a heavenly caramel layer beneath the fruit, adding sweetness and depth.
Pineapple rings (canned or fresh): The heroes of this dessert—you get a pop of color, juiciness, and tropical tang in every bite.
Maraschino cherries: These bright red gems turn each slice into a celebration and add a gentle burst of sweetness.
Graham cracker crumbs: The classic base that stays crisp and buttery, balancing the creamy filling above.
Granulated sugar: Sweetens both the crust and the velvety cheesecake, helping everything to brown and set perfectly.
Cream cheese (softened): The cheesecake’s foundation—make sure it’s really soft for the smoothest texture.
Eggs: The secret binding agent that helps the filling bake up rich and sliceable without cracking.
Vanilla extract: Rounds out the flavors and adds pure, comforting aroma.
Sour cream: Adds a bit of tang and keeps the cheesecake moist and luscious.
Crushed pineapple (well-drained): Intensifies that sunny pineapple flavor in every creamy bite—drain well to avoid a soggy filling.

How to Make Pineapple Upside-Down Cheesecake

Step 1: Prepare Your Pan

Start by preheating your oven to 325°F. Lightly grease a 9-inch springform pan and line the bottom with a parchment circle—this extra step guarantees a smooth, worry-free release later. Place the prepared pan on a baking sheet to catch any sneaky drips and save your oven from caramelized sugar cleanup!

Step 2: Make the Pineapple Topping

Pour that melted butter evenly over the parchment in your springform pan, then sprinkle the brown sugar right on top. Arrange the pineapple rings in a single, snug layer, then snuggle a maraschino cherry into the center of each ring for a cheerful, classic look.

Step 3: Mix and Press the Crust

In a medium bowl, stir together the graham cracker crumbs, granulated sugar, and melted butter until every crumb is coated and the mixture resembles wet sand. Gently press this mixture over the pineapple layer, working up the sides just a bit to create a beautiful edge and plenty of structure.

Step 4: Make the Cheesecake Filling

In a large bowl, beat the softened cream cheese until completely smooth—no lumps! Add the sugar and beat again until creamy and silky. Incorporate the eggs one at a time, mixing just until blended (don’t overdo it). Stir in the vanilla, sour cream, and well-drained crushed pineapple. The batter will be thick, glossy, and flecked with pineapple pieces.

Step 5: Assemble and Bake

Pour the cheesecake batter gently over the crust, spreading it evenly to the edges. Slide the pan (still on its baking sheet) into the oven and bake for 60 to 70 minutes. You’re looking for the center to be just set and the edges to turn lightly golden. Turn off the oven, crack the door, and let your cheesecake cool inside for 1 hour—this slow cooling helps prevent cracks and keeps the filling immeasurably creamy.

Step 6: Chill and Invert

After the hour in the oven, move your cheesecake to the fridge and let it chill for at least 4 hours (overnight is best for ideal texture and flavor). To serve, run a thin knife around the pan edge, carefully unlatch the springform, and invert the cheesecake onto a platter so the pineapple and cherry topping is front and center. Slice, serve chilled, and bask in the applause!

How to Serve Pineapple Upside-Down Cheesecake

Garnishes

Amp up the presentation of your Pineapple Upside-Down Cheesecake with a fluffy spray of whipped cream around the edge, a sprinkle of toasted coconut for crunch, or a dusting of grated lime zest to play up those tropical notes. Each garnish highlights different elements of the cheesecake and makes every slice look (and taste) extra-special.

Side Dishes

While this dessert is dazzling solo, you can dress up dessert time with light sides: a bowl of fresh berries complements the pineapple’s sweetness, or a scoop of vanilla ice cream creates an old-fashioned, soda-shop pairing. For a grown-up twist, a small glass of pineapple liqueur or a crisp, cold Prosecco is divine!

Creative Ways to Present

For parties, try serving the cheesecake in elegant individual jars—set a pineapple ring and cherry at the base, then layer in the crust and creamy filling. Or, if you’re feeling playful, cut the full cheesecake into bite-sized cubes, skewer them with cocktail picks, and serve as a cheerful tropical dessert platter!

Make Ahead and Storage

Storing Leftovers

Cover any leftover Pineapple Upside-Down Cheesecake tightly with plastic wrap or transfer slices to an airtight container. Store in the refrigerator for up to 5 days—the flavors stay luscious, and the texture remains beautifully creamy right through the week.

Freezing

Yes, you can freeze this cheesecake! Wrap individual slices or the whole cake (well-chilled and unmolded) tightly in plastic wrap, followed by a layer of aluminum foil. It will keep for up to 2 months in the freezer. Thaw overnight in the refrigerator for best results and optimal creaminess.

Reheating

Since cheesecakes are served chilled, reheating isn’t typically needed. But if you like your Pineapple Upside-Down Cheesecake slightly warm, microwave a slice for 10–15 seconds—just enough to soften the filling without melting the topping!

FAQs

Can I use fresh pineapple instead of canned?

Absolutely! Fresh, ripe pineapple tastes incredible here. Just slice into 1/2-inch rings and pat them dry before layering to prevent extra moisture, which can affect the topping’s texture.

How do I keep my cheesecake from cracking?

Don’t overmix the eggs, and let your Pineapple Upside-Down Cheesecake cool gradually as directed, first in the oven with the door cracked. That nice, slow cooling makes all the difference for a smooth top!

What’s the best way to invert the cheesecake without making a mess?

Chill it thoroughly, run a thin knife around the edge to release, then lay your serving plate upside-down atop the pan and flip them together in one confident motion. Gently remove the pan and the parchment—voilà, perfect topping!

Can I make Pineapple Upside-Down Cheesecake ahead of time?

Yes! In fact, it tastes even better when made a day ahead, as the flavors meld and the texture sets. Just keep it chilled and covered until serving time.

Is there a gluten-free option for the crust?

You bet—simply swap in gluten-free graham crackers or your favorite gluten-free cookie crumbs. Everything else in the recipe is naturally gluten-free, so nothing stands between you and that first blissful bite!

Final Thoughts

There’s something truly joyful about making and sharing Pineapple Upside-Down Cheesecake—it’s both a conversation starter and a guaranteed crowd-pleaser. Don’t hesitate to give it a try; I promise it’ll steal the show every time you bring it to the table!

Pineapple Upside-Down Cheesecake Recipe

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4.9 from 12 reviews

Author: admin
Total Time: 1 hour 40 minutes (plus chilling time)
Yield: 12 servings 1x
Diet: Non-Vegetarian

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Description

Indulge in the tropical flavors of a Pineapple Upside-Down Cheesecake. This delightful dessert combines the classic pineapple upside-down cake with a creamy cheesecake filling for a decadent treat that’s sure to impress.

Ingredients

Scale

Pineapple Topping:

1/4 cup unsalted butter, melted
1/2 cup brown sugar, packed
6–8 pineapple rings (canned or fresh)
6–8 maraschino cherries

Crust:

1 1/2 cups graham cracker crumbs
1/4 cup granulated sugar
1/3 cup unsalted butter, melted

Cheesecake Filling:

3 packages (8 ounces each) cream cheese, softened
1 cup granulated sugar
3 large eggs
1 teaspoon vanilla extract
1/2 cup sour cream
1/2 cup crushed pineapple, well-drained

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Instructions

Preheat oven to 325°F. Grease a 9-inch springform pan, line the bottom with parchment paper, and place on a baking sheet.
Prepare the topping: Pour melted butter in pan, sprinkle with brown sugar, arrange pineapple rings, and place cherries in the centers.
Make the crust: Combine graham cracker crumbs, sugar, and melted butter. Press mixture over pineapple layer and up the sides.
Create the filling: Beat cream cheese until smooth. Add sugar, eggs, vanilla, sour cream, and crushed pineapple. Pour over crust.
Bake for 60–70 minutes until set. Cool in the oven, then refrigerate for at least 4 hours.
Serve: Invert the cheesecake onto a plate, slice, and serve chilled.