Pineapple Upside Down Cheesecake

Alright, this Pineapple Upside Down Cheesecake? It’s the best of both worlds—classic pineapple upside down cake meets rich, creamy cheesecake. Imagine sweet caramelized pineapple and cherries on top, with a smooth vanilla cheesecake layer and buttery cake at the bottom. Every slice is bright, sweet, and totally irresistible.

I made it for a family dinner, and wow—it disappeared so fast! That tangy pineapple, gooey caramel, and silky cheesecake together? Absolute perfection in every bite. It looks fancy, but everyone will think you bought it from a bakery.

And guess what? It’s easier than it sounds. Just layer your fruit, whip up the cheesecake, bake, and chill. Let’s make it together—this is the kind of dessert that’ll steal the show at any gathering!

Why You’ll Love This Recipe

• A Two-in-One Classic: Instead of choosing between pineapple upside down cake and cheesecake, this recipe brings both into one dessert. The baked pineapple topping has that caramel-glazed look and flavor, while the cheesecake underneath offers richness and contrast.
• Balanced Texture and Sweetness: The graham cracker crust adds crunch, the pineapple topping brings syrupy tang, and the cheesecake is dense but smooth. The sweetness is present but not overpowering—just enough to satisfy.
• Make-Ahead Friendly: Like most cheesecakes, this one improves as it chills. You can—and should—make it the day before serving for best results.
• Reliable and Versatile: The steps are clear and achievable for intermediate home bakers. You don’t need to master cake folding or use specialty tools—just patience, good ingredients, and careful layering.

What You Need to Know Before You Start

Prep Time: 30 minutes
Cook Time: 1 hour 15 minutes
Cooling Time: 1 hour at room temperature
Chilling Time: At least 6 hours in the refrigerator (overnight is best)
Total Time: Approximately 8–9 hours (mostly inactive)

Servings: Makes 12 standard slices

Skill Level: Intermediate
You’ll need to bake the cheesecake in a water bath to prevent cracking and ensure even texture. It’s not difficult but requires careful handling of the springform pan (to avoid leaking) and patience during cooling and chilling stages.

Required Kitchen Tools

To ensure smooth preparation and baking, gather the following tools before you begin:

• 9-inch springform pan: Essential for easy unmolding and a clean final look. Line the bottom with parchment paper and wrap the outside in foil to prevent leaks.
• Roasting pan or large baking dish: Used to hold the water bath for gentle baking.
• Mixing bowls: Separate bowls for crust, topping, and cheesecake filling.
• Electric mixer: Hand or stand mixer works fine for creaming the cheesecake filling.
• Rubber spatula: Ideal for scraping bowls and smoothing batter.
• Measuring cups and spoons: Accuracy is important, especially in cheesecake recipes.
• Saucepan: Used to melt butter and sugar for the pineapple layer.
• Cooling rack: For air circulation and safe cooling of the baked cheesecake.
• Aluminum foil: Used to wrap the outside of the pan and help avoid leaks in the water bath.

Ingredients

For the Pineapple Topping

This is the glossy, caramelized fruit layer that will sit on top once the cheesecake is inverted.

• 7 tablespoons (98g) unsalted butter, melted and divided
  • 4 tablespoons are for melting with sugar to coat the pan. The remaining 3 tablespoons are mixed with graham crumbs for the crust.
• ½ cup (112g) packed light brown sugar
  • This combines with the melted butter to create a syrupy layer that caramelizes during baking.
• 10 canned pineapple slices, drained and patted dry (reserve the juice for the cheesecake layer)
  • Drying the pineapple prevents extra moisture from disrupting the topping or cheesecake texture.
• 13 maraschino cherries, drained and dried
  • These sit in the center of each pineapple ring and between gaps for color and added sweetness.

For the Crust

A classic graham cracker crust offers structure and crunch.

• 1 cup (134g) graham cracker crumbs
  • Use store-bought crumbs or pulse whole graham crackers in a food processor.
• 3 tablespoons (39g) granulated sugar
  • Adds a touch of sweetness to the crust.
• 3 tablespoons (42g) unsalted butter, melted
  • Binds the crumbs and helps them form a cohesive layer.

For the Cheesecake Filling

This creamy filling is rich, smooth, and lightly flavored with vanilla and pineapple juice to tie the layers together.

• 24 ounces (680g) full-fat cream cheese, softened to room temperature
  • Ensure it’s soft so it blends without lumps.
• 1 cup (225g) packed light brown sugar
  • Offers a more complex sweetness than white sugar and complements the topping.
• 3 tablespoons (24g) all-purpose flour
  • Adds just enough structure to the filling without making it cakey.
• ½ cup (115g) sour cream, room temperature
  • Contributes creaminess and helps lighten the texture slightly.
• 6 tablespoons pineapple juice, reserved from the canned pineapple
  • Infuses the cheesecake with a subtle fruity note without making it overpowering.
• 2 teaspoons pure vanilla extract
  • Rounds out the flavors and enhances the natural sweetness.
• 3 large eggs, at room temperature
  • Provide structure and richness; bring to room temp to avoid curdling the filling.

Variations for Pineapple Upside Down Cheesecake

While the base recipe is a classic, you can customize it depending on your preferences or ingredients you have on hand.

• Use Fresh Pineapple: If desired, substitute canned slices with thin rings of fresh pineapple. Just make sure to cook them briefly in a pan with a touch of sugar and water to soften them before using.
• Crust Swap: Instead of graham crackers, try shortbread cookie crumbs or vanilla wafers for a sweeter, buttery base.
• Add Coconut: Mix a few tablespoons of shredded sweetened coconut into the graham cracker crust or sprinkle over the pineapple before baking.
• Mini Cheesecakes: Make individual servings using a muffin tin lined with parchment circles. Adjust baking time accordingly (about 18–22 minutes).
• Spiced Filling: Add a pinch of ground ginger or cinnamon to the cheesecake filling to deepen the flavor.

How to Make Pineapple Upside Down Cheesecake

Step-by-Step Instructions

Step 1: Prepare the Springform Pan

1. Line the bottom of a 9-inch springform pan with parchment paper.
2. Wrap the outside of the pan in two layers of heavy-duty aluminum foil. This will protect the cheesecake from water during the water bath.
3. Lightly grease the inside of the pan with softened butter or non-stick spray.

Step 2: Make the Pineapple Topping

1. In a small saucepan, melt 4 tablespoons of unsalted butter over medium heat. Stir in the ½ cup brown sugar and let it melt and bubble for about 2 minutes until glossy and combined.
2. Pour the mixture into the prepared springform pan. Use a spatula to spread it evenly.
3. Arrange pineapple slices over the sugar-butter mixture, placing one in the center and the rest around it. Place a maraschino cherry in the middle of each ring, then fill in any gaps with the remaining cherries. Gently press them down so they adhere slightly to the sugar.

Step 3: Prepare the Crust

1. In a medium bowl, combine graham cracker crumbs, 3 tablespoons of sugar, and 3 tablespoons melted butter.
2. Mix until the crumbs are evenly moistened.
3. Gently press this mixture on top of the pineapple layer, spreading evenly but carefully so you don’t move the fruit.
4. Use the bottom of a flat glass or measuring cup to press down lightly to pack the crust.

Step 4: Make the Cheesecake Filling

1. In a large bowl, beat cream cheese with an electric mixer on medium speed until smooth and creamy—about 2 to 3 minutes.
2. Add the brown sugar and beat until fully incorporated.
3. Mix in the flour, then the sour cream, pineapple juice, and vanilla extract. Scrape down the sides of the bowl with a spatula.
4. Beat in the eggs, one at a time, on low speed. Mix just until combined—do not overbeat. The batter should be smooth but not whipped.

Step 5: Assemble and Bake

1. Carefully pour the cheesecake batter over the prepared crust and topping. Smooth the top with a spatula.
2. Tap the pan gently on the counter a few times to release any air bubbles.
3. Place the springform pan inside a large roasting pan. Fill the outer pan with hot water until it reaches halfway up the sides of the springform pan. This is your water bath, which helps prevent cracking and promotes even baking.
4. Bake at 325°F (163°C) for 70 to 75 minutes, or until the center is just set and slightly wobbly. The edges should be firm.

Step 6: Cool and Chill

1. Turn off the oven, crack the door slightly, and let the cheesecake cool in the oven for 1 hour. This gradual cooling helps prevent cracks.
2. Remove from the water bath and take off the foil. Cool the cheesecake on a wire rack until it reaches room temperature.
3. Cover and refrigerate for at least 6 hours, preferably overnight.

Step 7: Unmold and Invert

1. Once fully chilled, run a thin knife around the edge of the cheesecake to loosen it from the sides of the pan.
2. Release the springform latch and carefully remove the rim.
3. Place a serving plate upside down on top of the cheesecake. In one smooth motion, invert the cheesecake onto the plate so the pineapple layer is now on top.
4. Gently lift off the base and peel away the parchment paper.

Tips and Tricks for Success

• Dry Your Pineapple and Cherries Well: Excess moisture can cause soggy topping or dilute the caramel layer.
• Use Room Temperature Ingredients: This ensures a smooth batter without lumps.
• Avoid Overmixing the Eggs: Beating too much air into the batter can cause cracks during baking.
• Don’t Skip the Water Bath: It creates a humid environment, helping the cheesecake bake gently and evenly.
• Invert Carefully: If the cheesecake is well chilled and firm, it will invert easily without cracking. Take your time and do it in one motion.

Nutrition

Below is an approximate nutrition breakdown for one slice (based on 12 servings). Actual values may vary based on specific brands or ingredients used.

Nutrient	Amount per slice
Calories	420 kcal
Total Fat	28 g
Saturated Fat	16 g
Cholesterol	120 mg
Sodium	260 mg
Carbohydrates	38 g
Sugar	30 g
Fiber	1 g
Protein	6 g
Calcium	100 mg

Pineapple Upside Down Cheesecake FAQs

Can I use fresh pineapple instead of canned?
Yes. Just slice the pineapple into thin rounds and cook them briefly in a skillet with a little sugar to soften. Make sure they are well-drained and patted dry before using.

Do I have to bake this in a water bath?
Yes. The water bath (also called a bain-marie) helps ensure even baking and prevents cracking. It’s especially important for dense cheesecakes like this one.

Why does my cheesecake crack?
Common reasons include overmixing the eggs, baking at too high a temperature, or skipping the water bath. Gradual cooling also helps prevent cracks.

Can I freeze this cheesecake?
Yes. Wrap individual slices tightly in plastic wrap and foil, then freeze for up to 2 months. Thaw overnight in the refrigerator before serving.

How long will leftovers keep?
Stored in an airtight container in the fridge, this cheesecake keeps well for up to 4–5 days.

Conclusion

This Pineapple Upside Down Cheesecake offers a show-stopping presentation and a satisfying blend of tropical fruit and creamy cheesecake. Whether you’re making it for a special occasion or simply want to try something new, it’s a dessert worth the effort. Each layer contributes to a balanced bite, and with proper cooling and handling, the results are reliably beautiful and delicious.