If ever there was a show-stopping dessert designed to deliver pure sunshine and smiles, it’s the Pineapple Upside-Down Cheesecake Cake. This beauty marries the iconic caramelized pineapple cake of your childhood with a lusciously creamy cheesecake layer—and trust me, the combination is downright irresistible. Each bite gives you a burst of sweet-tangy pineapple, buttery cake, and rich cheesecake, crowned with glossy cherries and the golden hue of nostalgia. It’s a celebration in every slice—just the dish for birthdays, summer gatherings, or anytime you want to treat yourself to something truly special!

Pineapple Upside-Down Cheesecake Cake Recipe - Recipe Image

Ingredients You’ll Need

Let’s talk ingredients! Each one brings something special to the Pineapple Upside-Down Cheesecake Cake, creating that perfect balance of sweet, tangy, creamy, and moist. Don’t worry, these are all easy to find—and they all play a star role in taste, texture, or color.

Unsalted butter (¼ cup, melted): Gives the pineapple topping its rich, golden base and keeps things ultra moist.
Packed brown sugar (½ cup): Creates that classic caramelized sweetness and glossy, sticky topping we all crave.
Canned pineapple rings (7–8): Delivers tropical flavor and signature presentation—go for slices packed in juice for best taste.
Maraschino cherries (optional): A classic retro touch—nestle one in each ring for color and a juicy pop.
Yellow cake mix (1 box): The reliable, fluffy foundation for our pineapple crown and cheesecake throne.
Eggs, oil, and water (as listed on cake mix box): Brings your cake layer to life (check the box for amounts—usually 3 eggs, oil, and water).
Cream cheese (16 oz, softened): The soulmate to pineapple; creates the smooth, tangy cheesecake layer.
Granulated sugar (½ cup): Sweetens and balances the tang of the cream cheese beautifully.
Eggs (2 large): Essential for structure and creaminess in the cheesecake.
Sour cream (½ cup): Adds luxurious creaminess and a slight tang that makes your cheesecake unforgettable.
Vanilla extract (1 teaspoon): Enhances all the flavors, especially the cheesecake’s.
All-purpose flour (1 tablespoon): Helps the cheesecake set up nice and sturdy for layering.

How to Make Pineapple Upside-Down Cheesecake Cake

Step 1: Prepare the Cheesecake Layer

Begin by preheating your oven to 325°F (165°C). Line a 9-inch springform pan with parchment and lightly grease the sides for easy release. In a large bowl, blend softened cream cheese with sugar until velvety smooth—no lumps! Beat in the eggs, one at a time (this keeps your cheesecake silky). Stir in the sour cream, vanilla, and a tablespoon of flour for structure. Pour this creamy batter into your pan and bake for 35 to 40 minutes, just until it’s set (a slight wobble in the center is perfect). When done, cool the cheesecake completely, then chill for at least 4 hours (or overnight, if you’re planning ahead). Cold cheesecake will be easier to handle and layer.

Step 2: Make the Pineapple Topping and Cake Layer

Now, turn your attention to the cake layer—raise the oven temperature to 350°F (175°C). Grab a 9-inch round cake pan and grease it well. Pour in the melted butter and swirl to completely coat the bottom. Sprinkle brown sugar evenly over the butter for a luscious base, then arrange the pineapple rings across the sugar. For that classic look, pop a cherry into the center of each ring. Mix up the yellow cake batter following the box instructions (typically just a few pantry staples like eggs, water, and oil). Carefully pour this batter over the arranged fruit—spread gently so you don’t disturb your beautiful topping. Bake for 30 to 35 minutes until a toothpick comes out with a few moist crumbs. Let the cake cool in the pan for 10 minutes so that caramelized topping gets set.

Step 3: Assemble the Pineapple Upside-Down Cheesecake Cake

Once your cake is cooled and your cheesecake is thoroughly chilled, it’s time for the magic! Invert the pineapple cake onto your serving plate so the golden fruit and cherries are on top. Carefully lift the cheesecake layer out of its pan (a chilled or slightly frozen cheesecake layer makes this part easier). Gently center the cheesecake on top of the pineapple cake. If you have any little gaps along the edge, you can smooth them out with a bit of whipped cream or extra frosting. Pop the whole cake in the fridge for an hour to help it set and for the flavors to mingle. Slice it up and admire those layers!

How to Serve Pineapple Upside-Down Cheesecake Cake

Garnishes

This cake looks gorgeous straight out of the pan, but you can take it up a notch! Try a dollop of freshly whipped cream, a handful of toasted coconut flakes, or even a drizzle of pineapple syrup over each slice. For special occasions, a few extra cherries on the plate or some finely grated lime zest will pop both visually and flavor-wise.

Side Dishes

Since the Pineapple Upside-Down Cheesecake Cake is wonderfully rich and fruity, I love serving it with light, fresh accompaniments. Consider a bowl of mixed berries, a scoop of coconut sorbet, or a citrusy fruit salad. These refreshing sides will balance the cake’s decadent, creamy layers perfectly.

Creative Ways to Present

If you’re in the mood to wow your guests, cut the cake into elegant wedges and plate each with a swirl of whipped cream and a sprig of mint. For parties, you can even bake individual mini versions in small springform pans—the wow factor is built-in! Or, try serving with pineapple-infused cocktails for a tropical twist.

Make Ahead and Storage

Storing Leftovers

Keep any leftover Pineapple Upside-Down Cheesecake Cake covered in the fridge. The cake is just as delicious for up to four days after assembly, and the flavors seem to meld and get even better overnight. Store slices in an airtight container or wrap tightly with plastic wrap to keep them from drying out.

Freezing

You can absolutely freeze this cake, but be sure to chill it thoroughly first. Wrap individual slices or the whole cake tightly in plastic wrap and then in foil. It will keep beautifully for up to two months. To serve, just thaw in the refrigerator overnight and enjoy!

Reheating

Because of the cheesecake layer, this treat is best enjoyed cold or at cool room temperature. If you prefer a slightly warmer cake, let a slice sit at room temperature for 30 minutes before serving. Avoid microwaving—it can make the texture rubbery and disturb the decorative topping.

FAQs

Can I use fresh pineapple for Pineapple Upside-Down Cheesecake Cake?

Yes, you can! Just be sure to slice the fresh pineapple thinly so it cooks evenly and still caramelizes beautifully. If using fresh pineapple, you might want to soften the rings briefly in a skillet with a little butter and sugar before arranging them in the pan.

How do I prevent the cheesecake from cracking?

Make sure not to overbeat the cheesecake batter once you add the eggs, and bake it just until barely set. Also, allow the cheesecake to cool gently in the turned-off oven with the door ajar before chilling—it helps prevent cracks!

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

Absolutely! Substitute a gluten-free cake mix for the standard one, and double-check that your flour and other ingredients are certified gluten-free. The rest of the recipe remains the same.

What if I don’t have a springform pan?

If you don’t have a springform pan for the cheesecake layer, you can use a regular 9-inch cake pan lined well with parchment, but be extra cautious when releasing the cheesecake to prevent it from sticking or breaking.

Can I make this cake ahead of time?

Yes! You can fully assemble the Pineapple Upside-Down Cheesecake Cake a day in advance and store it tightly covered in the fridge. In fact, the flavors meld and slice even more cleanly after a restful night in the refrigerator.

Final Thoughts

If you’re looking for a dessert that guarantees gasps and happy faces, the Pineapple Upside-Down Cheesecake Cake will deliver every single time. It’s the perfect blend of old-school charm and creamy decadence, wrapped up in a sunshiny, vibrant package. Don’t wait for a big occasion—invite this beauty into your kitchen and create a new favorite tradition!

Pineapple Upside-Down Cheesecake Cake Recipe

5 Stars 4 Stars 3 Stars 2 Stars 1 Star

4.5 from 25 reviews

Author: admin
Total Time: 6 hours (including chilling and cooling)
Yield: 12 slices 1x
Diet: Vegetarian

Print Recipe

Description

Indulge in the delightful combination of a classic pineapple upside-down cake and a creamy cheesecake with this Pineapple Upside-Down Cheesecake Cake. Layers of moist yellow cake, sweet pineapple, and a rich cheesecake filling come together for a decadent dessert that is sure to impress.

Ingredients

Scale

For the Pineapple Topping:

1/4 cup unsalted butter, melted
1/2 cup packed brown sugar
7–8 canned pineapple rings
Maraschino cherries (optional, for center of rings)

For the Cake Layer:

1 box yellow cake mix (plus ingredients listed on the box: eggs, oil, water)

For the Cheesecake Layer:

16 oz cream cheese, softened
1/2 cup granulated sugar
2 large eggs
1/2 cup sour cream
1 teaspoon vanilla extract
1 tablespoon all-purpose flour

Cook Mode Prevent your screen from going dark

Instructions

Make the Cheesecake Layer: Preheat oven to 325°F (165°C). Line the bottom of a 9-inch springform pan with parchment paper and lightly grease the sides. In a large bowl, beat the cream cheese and sugar until smooth. Add eggs one at a time, then mix in sour cream, vanilla, and flour until fully combined. Pour into prepared pan and bake for 35–40 minutes until just set. Cool completely, then refrigerate for at least 4 hours or overnight.
Prepare the Pineapple Base and Cake Layer: Preheat oven to 350°F (175°C). Grease a 9-inch round cake pan. Pour melted butter into the pan and swirl to coat the bottom. Evenly sprinkle the brown sugar over the butter. Arrange pineapple rings over the sugar and place a maraschino cherry in the center of each if desired. Prepare the yellow cake mix according to package directions. Gently pour the batter over the pineapples, spreading evenly. Bake for 30–35 minutes or until a toothpick inserted into the center comes out clean. Cool for 10 minutes in the pan.
Assemble the Cake: Once both layers are completely cooled, invert the pineapple cake onto a serving plate so the fruit side is up. Carefully place the chilled cheesecake layer on top. Press down lightly and smooth any gaps with extra frosting or whipped cream if desired. Refrigerate for 1 hour before slicing.