Pineapple Upside Down Cheesecake: A Tropical Twist on a Creamy Classic

Golden pineapple rings, sticky caramelized brown sugar, and buttery cake usually steal the show in a classic pineapple upside-down dessert. But this time, cheesecake takes center stage. Pineapple Upside Down Cheesecake blends two iconic treats into one dreamy dessert with bold flavor and rich texture. Sweet tropical fruit balances the tangy creaminess of the cheesecake, while a caramel-drizzled topping adds just the right amount of indulgence.

This cake delivers beauty and boldness with every slice. The fruit glistens like stained glass, anchored by a thick, velvety cheesecake layer that melts on the tongue. One bite brings summer to your taste buds—even in the middle of winter. Each forkful promises crunch, cream, and citrusy brightness.

Dessert lovers don’t have to pick between fruity and creamy anymore. This showstopper offers both in one glorious bake. It turns any gathering into a celebration and leaves your guests reaching for seconds.

Ingredients

For the Pineapple Topping:

¼ cup (60g) unsalted butter, melted
½ cup (100g) packed light brown sugar
6–7 canned pineapple slices (drained, reserve juice)
6–8 maraschino cherries

For the Cheesecake Layer:

3 (8 oz) packages cream cheese, softened
¾ cup (150g) granulated sugar
1 tsp vanilla extract
3 large eggs
½ cup (120ml) sour cream
2 tbsp pineapple juice (from the can)

For the Cake Layer:

½ cup (115g) unsalted butter, softened
¾ cup (150g) granulated sugar
2 large eggs
1 tsp vanilla extract
1½ cups (190g) all-purpose flour
1½ tsp baking powder
¼ tsp salt
½ cup (120ml) whole milk

Equipment Needed:

9-inch springform pan (for the cheesecake layer)
9-inch round cake pan (for the pineapple upside-down base)
Mixing bowls (at least 2 large)
Electric hand mixer or stand mixer
Rubber spatula
Whisk
Measuring cups and spoons
Cooling rack
Offset spatula or butter knife (to smooth layers and loosen sides)
Baking sheet (to place under the springform pan to catch drips)
Parchment paper (optional, for easy removal)
Aluminum foil (to wrap pan and prevent leaks in water bath, if used)

Step By Step Guide Of Pineapple Upside Down Cheesecake

Step 1: Prepare the Pineapple Topping

Melt ¼ cup of butter and pour it evenly into the bottom of a 9-inch round cake pan. Sprinkle ½ cup of brown sugar over the melted butter. Arrange pineapple slices in a single layer on top of the sugar mixture, and place a maraschino cherry in the center of each ring. Set aside.

Step 2: Preheat Your Oven

Preheat your oven to 325°F (163°C). Place a large baking sheet on the bottom rack to catch any drips from the springform pan later.

Step 3: Make the Cheesecake Batter

In a large bowl, beat softened cream cheese with a hand or stand mixer until smooth. Add granulated sugar and mix until combined. Add vanilla, eggs (one at a time), sour cream, and pineapple juice. Beat until creamy and lump-free. Set aside.

Step 4: Bake the Cheesecake Layer

Line the bottom of a springform pan with parchment paper and pour in the cheesecake batter. Smooth the top. Bake for 45–50 minutes, or until the center is set but slightly jiggly. Remove from the oven and let it cool completely, then refrigerate for at least 4 hours or overnight.

Step 5: Make the Cake Batter

Cream the softened butter and granulated sugar in a clean mixing bowl until fluffy. Add eggs one at a time, then vanilla. In a separate bowl, whisk together flour, baking powder, and salt. Add the dry ingredients to the wet mixture, alternating with milk. Mix just until combined.

Step 6: Assemble the Layers Before Final Baking

Once the cheesecake has fully chilled and set, gently remove it from the springform pan. Place it over the prepared pineapple topping in the round cake pan. Carefully spread the cake batter on top of the cheesecake, smoothing it out evenly.

Step 7: Bake the Assembled Cake

Bake the entire assembled cake in the preheated oven at 325°F (163°C) for 50–60 minutes. Check for doneness by inserting a toothpick into the cake layer—it should come out clean. If the top browns too quickly, loosely cover it with foil.

Step 8: Cool the Cake Properly

Remove the cake from the oven and allow it to cool in the pan for 20 minutes. This rest time helps the cake set and makes it easier to flip without falling apart.

Step 9: Flip and Unmold the Cake

Place a serving plate or cake stand over the top of the cake pan. Carefully flip the pan over and gently lift it off to reveal the beautiful pineapple topping. If any fruit sticks to the pan, simply place it back on the cake.

Step 10: Chill and Serve

Refrigerate the cake for at least 1 hour before serving. This helps the cheesecake and cake layers hold their shape. Slice with a warm knife for clean edges and serve chilled or slightly room temp.

Serving Tips

1. Chill Before Slicing

For the cleanest slices, chill the cake for at least 1–2 hours before serving. A firm cheesecake layer holds its shape better when cold.

2. Use a Warm Knife

Dip a sharp knife into hot water and wipe it dry before each cut. This prevents dragging and keeps each slice neat and professional-looking.

3. Add a Tropical Garnish

Top each slice with a dollop of whipped cream, a mint leaf, or extra pineapple chunks for a fresh, festive touch.

4. Pair with Coffee or Coconut Cream

Serve with a cup of bold coffee or a drizzle of coconut cream for a dessert that feels like a tropical vacation.

5. Serve Slightly Chilled

Although best served cold, you can let it sit out for 10–15 minutes before serving to soften slightly and enhance the flavor balance.

FAQs

1. Can I use fresh pineapple instead of canned?

Yes, fresh pineapple works beautifully. Just slice it thin and remove the core from each ring. Make sure to pat it dry to reduce extra moisture.

2. Do I need a water bath for the cheesecake?

A water bath isn’t required but can help prevent cracks. If you want a super-smooth finish, wrap the springform pan in foil and bake it in a water bath.

3. How long does Pineapple Upside Down Cheesecake last in the fridge?

It stays fresh for up to 4–5 days in an airtight container in the refrigerator. The texture remains great during this time.

4. Can I freeze this cheesecake?

Yes, but only freeze the cheesecake layer or fully assembled cake without the pineapple topping. Wrap tightly and freeze for up to 1 month. Add the topping fresh before serving.

5. Why is my pineapple topping sticking to the pan?

This usually happens if the pan isn’t greased well or the sugar wasn’t spread evenly. Make sure to grease thoroughly and cool the cake slightly before flipping.

Conclusion

Pineapple Upside Down Cheesecake brings together the rich creaminess of cheesecake and the fruity, caramel-kissed charm of a classic pineapple upside-down cake. It’s bold, beautiful, and surprisingly simple to make. Whether you’re hosting a summer brunch or celebrating a special occasion, this dessert will turn heads and win hearts. One bite, and you’ll understand why it’s worth every layer.

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