Pineapple Upside-Down Cheesecake Cake Recipe

If you’re ready to wow your taste buds with a luscious fusion of creamy and tropical flavors, get ready to fall in love with Pineapple Upside-Down Cheesecake Cake! This whimsical dessert brings together the nostalgic beauty of a classic pineapple upside-down cake and the decadence of velvety cheesecake, creating a showstopping treat perfect for celebrations or just because. Silky cheesecake sits sandwiched between layers of buttery cake and caramelized pineapple, all topped with vibrant maraschino cherries. Trust me, this is the kind of dessert that gets everyone at the table talking — and going back for seconds!

this Recipe

Ingredients You’ll Need

With a handful of everyday basics and a few standout tropical stars, every ingredient in this recipe plays a special role. Whether it’s creating an irresistibly tender crumb or balancing tangy sweetness, here’s what you need for Pineapple Upside-Down Cheesecake Cake:

• Unsalted butter: Adds luscious richness to both the pineapple and cake layers, and helps achieve that golden caramelized topping.
• Brown sugar: The foundation of the signature upside-down caramel, giving a deep, molasses flavor that seeps into the pineapple.
• Canned pineapple slices: These not only provide bold tropical flavor, but their juices also infuse both the cake and the topping.
• Maraschino cherries: Classic for adding jewel-like pops of color and a touch of sweetness on top.
• Cream cheese: The heart of the cheesecake layer; always use full-fat, room temperature for smoothest results.
• Granulated sugar: Sweetens both cheesecake and cake layers without overwhelming them.
• Eggs: Give structure and richness to the cheesecake and cake, ensuring everything holds together beautifully.
• Vanilla extract: Rounds out flavors in both the cheesecake and cake layers for extra depth.
• Sour cream: Adds a subtle tang and creamy texture to the cheesecake.
• All-purpose flour: Essential for a tender, sturdy cake layer that supports the stacked dessert.
• Baking powder: Ensures the cake rises perfectly light and fluffy.
• Salt: Balances sweetness and enhances every other flavor.
• Whole milk: Adds moisture and richness, keeping the cake soft and delectable.
• Pineapple juice: Reserved from the can — this infuses the cake batter with even more sunny pineapple flavor.

How to Make Pineapple Upside-Down Cheesecake Cake

Step 1: Prepare the Pineapple Layer

Start by preheating your oven to 325°F and lining a 9-inch springform pan with parchment paper for easy release later. Pour your melted butter into the bottom and sprinkle the brown sugar evenly. Now, gently arrange the pineapple slices in a beautiful fan or circle pattern, nestling maraschino cherries in the centers. This foundation becomes the gloriously glossy crown once your cake is flipped, so have fun with the design!

Step 2: Mix the Cheesecake Layer

Using an electric mixer, beat the softened cream cheese and granulated sugar together until smooth and creamy. Add the eggs, one at a time, mixing well after each. Blend in vanilla extract and sour cream for an extra hint of tartness and silkiness. Pour this dreamy cheesecake batter over the arranged fruit — try not to disturb your perfect pineapple pattern! Smooth the top out and let this layer bake for about 25 minutes, just until it’s set but still with a gentle wobble in the center.

Step 3: Cool the Cheesecake Base

After the cheesecake layer has set in the oven, take it out and let it cool slightly. This pause is crucial – it helps keep your layers distinct and prevents the cake from sinking. A brief rest at room temperature ensures the cheesecake provides that delicate, creamy “middle” that makes this Pineapple Upside-Down Cheesecake Cake so unforgettable.

Step 4: Whip Up the Cake Layer

While the cheesecake base cools, whisk together the flour, baking powder, and salt in one bowl. In another bowl, cream together unsalted butter and granulated sugar until it’s light and fluffy — this step makes the cake layer oh-so-springy. Beat in the eggs, then the vanilla extract. Alternate adding your dry mixture with the milk and reserved pineapple juice, blending until you get a smooth, thick batter full of tropical aroma.

Step 5: Assemble and Bake the Cake

Gently spread the cake batter over the cheesecake layer — don’t rush, as you want to keep those gorgeous layers distinct. Once assembled, return the pan to your oven and bake for 45 to 50 minutes. The cake is ready when a toothpick poked into the top comes out clean and the surface is golden brown. Resist the urge to flip immediately! Let it cool completely in the pan so those glorious layers have time to settle.

Step 6: Invert, Chill, and Serve

Once fully cooled, carefully unclip the springform pan and invert your cake onto a serving plate. The magic reveal: candied pineapples and glossy cherries glistening atop your masterpiece! For absolute best results, chill the finished Pineapple Upside-Down Cheesecake Cake for at least two hours — overnight is even better — so every bite slices cleanly and the flavors have a chance to meld beautifully.

How to Serve Pineapple Upside-Down Cheesecake Cake

Garnishes

For a burst of elegance, add a few extra maraschino cherries or tuck some fresh pineapple wedges beside each slice. A little dusting of powdered sugar or a swoosh of sweetened whipped cream is always welcome. For tropical flair, sprinkle with toasted coconut flakes or a few bright mint leaves.

Side Dishes

This cake truly shines solo, but if you want to make dessert extra-memorable, serve it with a scoop of coconut or vanilla ice cream. Pairing with a lightly tart fruit salad or a dollop of tangy Greek yogurt helps offset the sweetness and brings in a refreshing twist.

Creative Ways to Present

Pineapple Upside-Down Cheesecake Cake deserves to be shown off! Place it proudly on a cake stand for a party, or slice and layer the servings into parfait glasses for an individual trifle-style dessert. For brunch, serve tiny wedges alongside mugs of coffee and arrange edible flowers for a bright, sunny scene.

Make Ahead and Storage

Storing Leftovers

To keep your Pineapple Upside-Down Cheesecake Cake moist and fresh, cover any leftovers with plastic wrap or store in an airtight container in the fridge. It will stay delicious and flavorful for up to four days without losing its dreamy texture.

Freezing

If you find yourself with extra slices (lucky you!), this cake actually freezes quite well. Cut into individual portions, wrap them tightly in plastic wrap, then in foil, and tuck them in the freezer for up to two months. Thaw overnight in the refrigerator before enjoying again.

Reheating

There’s no need to warm up Pineapple Upside-Down Cheesecake Cake; in fact, it’s best served chilled for clean slices and maximum flavor. But if you prefer it slightly warm, let a slice rest at room temperature for 15–20 minutes, or give it a quick, gentle zap in the microwave for a few seconds (not too long or the cheesecake may soften too much).

FAQs

How do I avoid the cake sticking to the pan?

Using a parchment-lined and well-greased springform pan is key for easy release. Let the cake cool completely so everything holds together, and run a thin knife around the edges before unclipping the pan for a stress-free unmolding experience.

Can I use fresh pineapple instead of canned?

Absolutely! Fresh pineapple adds a beautiful flavor, just be sure to pat the slices well so they aren’t too juicy. For that signature sweetness and moisture in the batter, use additional pineapple juice (or a touch more sugar if needed).

What’s the best way to get clean slices?

Chill the cake thoroughly, then use a sharp knife dipped in hot water and wiped dry between each cut. This gives you those beautifully neat, bakery-style wedges every time.

Can I make Pineapple Upside-Down Cheesecake Cake gluten-free?

Yes! Simply swap in your favorite 1:1 gluten-free baking flour for the all-purpose flour, and make sure the baking powder is gluten-free as well. The rest of the ingredients are naturally gluten-free.

Do I really need to chill the cake before serving?

Chilling isn’t mandatory, but it’s highly recommended! This resting period helps the flavors blend, sets the cheesecake layer, and makes the cake easier to slice for picture-perfect pieces.

Final Thoughts

If you’re looking to make a memorable, crowd-pleasing dessert that’s both comforting and novel, Pineapple Upside-Down Cheesecake Cake is your new secret weapon. It’s a party on a plate, effortless to serve, and oh-so-worthy of a special spot in your baking rotation. Give it a try — your friends and family will thank you!

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