Sometimes, combining two beloved desserts into one is the best idea. This Pineapple Upside Down Cheesecake has all the best elements from both: the rich, creamy smoothness of a cheesecake and the sweet, caramelized goodness of a classic pineapple upside-down cake.
The balance of tangy cream cheese and the juicy, golden pineapple creates a dessert that’s both comforting and indulgent.
Plus, with just the right amount of brown sugar and butter to create that signature caramelization, each bite is like a mini tropical vacation.
It’s the kind of treat you want to pull out at family gatherings or for a special weekend dessert—where every slice is sure to be the star of the show.
Both desserts offer that perfect combination of creamy texture and sweet, caramelized richness.
What’s so Special About This Dish?
- Texture: Smooth, creamy cheesecake meets the satisfying bite of soft, caramelized pineapple.
- Flavor: Tangy cream cheese balanced with the sweet, rich notes of pineapple and brown sugar.
- Aromas: The subtle scent of vanilla mixed with the tropical aroma of pineapple fills the kitchen.
Pineapple Upside down Cheesecake Recipe
Equipment
- 9-inch springform pan
- Mixing bowls
- Electric mixer
- Whisk
- Spatula
- Knife for slicing pineapple
- Measuring cups and spoons
- Small saucepan
Ingredients
Pineapple Compote
- 6 cups pineapple rings quartered
- 1 and 1/4 cups pineapple juice
- 2/3 cup + 1 tbsp dark brown sugar packed 300 grams
- 2 tbsp + 1 tsp corn starch
- 2 tbsp + 1 tsp water
- 2 tsp vanilla extract
- 2-3 tbsp vanilla rum or coconut rum optional
For the Crust:
- 3 cups graham cracker crumbs
- 1/2 cup salted butter melted
For the Cheesecake Batter
- 32 ounces full fat cream cheese softened at room temperature 906 grams
- 1 and 1/2 cups brown sugar 330 grams
- 4 large eggs at room temperature
- 3/4 cup full fat sour cream at room temperature 180 grams
- 2 tsp vanilla extract
For the Whipped Cream
- 4 tsp cold water
- 1 tsp plain powdered gelatin
- 1 cup heavy whipping cream
- 1/4 cup + 2 tbsp powdered sugar
- 2 tsp vanilla extract
For Decorating:
- maraschino cherries
Instructions
- Make Pineapple Filling/Topping: Stir cornstarch and water until dissolved. In a saucepan, cook pineapple chunks, brown sugar, and pineapple juice over high heat for 18-25 minutes until liquid reduces to a syrupy consistency. Add cornstarch slurry and cook for 1-2 minutes until thickened. Stir in vanilla and rum, then cool in the fridge.
- Make Crust: Preheat oven to 350°F. Spray a 9-inch springform pan and line the bottom with parchment paper. Mix melted butter with graham crumbs and press into the pan. Bake for 10 minutes and set aside.
- Make Cheesecake Filling: Beat softened cream cheese with sugar until creamy. Add eggs one at a time, then mix in vanilla, sour cream, and rum. Stir until smooth.
- Prepare Water Bath: Boil water in a large pot. Place the springform pan inside a 10-inch cake pan, then set in a roasting pan. Pour boiling water into the roasting pan until it reaches 2 inches deep.
- Assemble Cheesecake: Pour half the cheesecake batter into the pan. Add 1/3 of the pineapple filling. Pour the remaining batter on top and smooth out.
- Bake Cheesecake: Bake at 350°F for 1 hour 25 minutes to 1 hour 45 minutes. The center should have a slight wobble, and the knife should come out clean from the edge. Let cool in the oven for 1 hour.
- Cool Cheesecake: Remove from the oven and let cool to room temperature. Refrigerate for at least 6 hours or up to 1 day.
- Make Whipped Cream: Dissolve gelatin in water and microwave for 5 seconds. Beat whipped cream ingredients, then add gelatin mixture. Beat until stiff peaks form.
- Serve Cheesecake: Remove the cheesecake from the springform pan. Top with pineapple topping and whipped cream. Garnish with maraschino cherries.
- Store Leftovers: Store leftovers in an airtight container in the fridge for 3-4 days.
Nutrition Info:
| Nutrition | Value |
| Calories | 804kcal |
| Carbohydrates | 86g |
| Cholesterol | 190mg |
| Fat | 0.3g |
| sugar | 69g |
| Sodium | 484mg |
Tips for the Perfect Pineapple Upside-Down Cheesecake!
- Choose the Right Pineapple: Use canned pineapple rings for convenience, but if you prefer fresh pineapple, ensure it’s ripe and sweet. For fresh pineapple, cook slightly longer to soften it and bring out its natural sugars.
- Proper Crust Technique: Press the graham cracker crust firmly and evenly into the pan to prevent crumbling when sliced. Use the bottom of a measuring cup for a smooth, compact base.
- Avoid Lumpy Cheesecake Batter: Use softened cream cheese and room-temperature eggs and sour cream. This ensures a smooth batter without clumps. Beat cream cheese and sugar first to remove lumps before adding other ingredients.
- Prevent Cracks with a Water Bath: The water bath creates gentle, even heat, reducing the risk of cracks in your cheesecake. Wrapping the springform pan tightly with foil or using a cake pan barrier keeps water from seeping into the crust.
- Cool Gradually: Let the cheesecake cool in the oven with the door cracked open for an hour before moving it to room temperature. This gradual cooling helps prevent sinking or cracking.
- Thickened Pineapple Filling: Don’t skip the cornstarch slurry! It thickens the pineapple topping to a syrupy consistency, keeping it from becoming too watery when added to the cheesecake.
Joe Miller is the passionate founder of Food Landscape Insight, where he shares his love for cooking and culinary experiences. Growing up in a family-run diner, Joe was immersed in the vibrant world of food from an early age. The kitchen became his canvas, and food, his way of storytelling.
Through years of experimentation and learning, Joe honed his skills and started his blog to inspire others to embrace the joy of cooking. Each recipe he shares is a blend of tradition, creativity, and the heartfelt memories that food brings to life, all with the aim of fostering a deeper connection to food.
