Pineapple Upside-Down Cheesecake

If you love classic pineapple upside-down cake and rich, creamy cheesecake, this Pineapple Upside-Down Cheesecake is the ultimate dessert. A buttery graham cracker crust is topped with a silky smooth cheesecake filling and finished with a beautiful layer of caramelized pineapple rings and bright maraschino cherries. As it bakes, the brown sugar and butter create a glossy caramel glaze that soaks into the pineapple, giving every bite the perfect balance of creamy, fruity, and buttery flavors. This stunning dessert is ideal for holidays, birthdays, family gatherings, potlucks, or any special occasion. Despite its impressive appearance, it’s surprisingly easy to make with simple ingredients and a little patience. Chilled until perfectly set, each slice is rich, smooth, and packed with tropical sweetness that will have everyone asking for a second piece.

Ingredients For the Pineapple Topping

• ¼ cup unsalted butter, melted
• ½ cup packed light brown sugar
• 8–10 pineapple rings (canned, drained)
• 8–10 maraschino cherries, drained

For the Graham Cracker Crust

• 2 cups graham cracker crumbs
• ⅓ cup granulated sugar
• ½ cup unsalted butter, melted

For the Cheesecake Filling

• 24 ounces (680 g) cream cheese, softened
• 1 cup granulated sugar
• 3 large eggs
• 1 teaspoon vanilla extract
• ½ cup sour cream
• 2 tablespoons cornstarch
• ¼ teaspoon salt

Step-by-Step Instructions

Step 1: Prepare the Pan

Preheat your oven to 325°F (163°C). Grease a 9-inch springform pan and wrap the outside tightly with aluminum foil if using a water bath.

Step 2: Make the Pineapple Layer

Pour the melted butter into the bottom of the pan and spread it evenly. Sprinkle the brown sugar over the butter. Arrange the pineapple rings neatly on top, placing a maraschino cherry in the center of each pineapple ring.

Step 3: Prepare the Crust

In a medium bowl, combine the graham cracker crumbs, sugar, and melted butter until the mixture resembles wet sand. Carefully press the crumb mixture over the pineapple layer and slightly up the sides of the pan. Chill the crust for 10 minutes while preparing the filling.

Step 4: Prepare the Cheesecake Filling

Using a large mixing bowl, beat the softened cream cheese until completely smooth and creamy. Add the sugar and continue mixing until fully incorporated. Beat in the eggs one at a time, mixing on low speed after each addition. Stir in the vanilla extract, sour cream, cornstarch, and salt until the batter is silky smooth. Avoid overmixing to prevent air bubbles.

Step 5: Assemble

Gently pour the cheesecake filling over the prepared crust and smooth the top with a spatula.

Step 6: Bake

Bake for 60–70 minutes, or until the edges are set while the center still has a slight jiggle. Turn off the oven, crack the oven door slightly, and allow the cheesecake to cool inside for 1 hour.

Step 7: Chill

Remove the cheesecake from the oven and refrigerate for at least 6 hours, preferably overnight, until completely set.

Step 8: Unmold and Serve

Run a thin knife around the edge of the pan before releasing the springform ring. Carefully invert the cheesecake onto a serving plate so the pineapple topping is on top. Slice with a warm knife, wiping it clean between each cut for neat slices.

Tips & Notes

• Drain the pineapple rings well to prevent excess moisture.
• Bring the cream cheese, eggs, and sour cream to room temperature for the smoothest filling.
• Mix on low speed to reduce cracks.
• A water bath helps the cheesecake bake evenly and creates a creamier texture.
• Refrigerating overnight produces the best flavor and texture.
• Garnish with whipped cream or toasted coconut for an extra-special presentation.
• Store covered in the refrigerator for up to 5 days.

Frequently Asked Questions

Can I use fresh pineapple?
Yes, but canned pineapple rings hold their shape better and provide more consistent sweetness.

Why did my cheesecake crack?
Overmixing the batter or overbaking are the most common causes. Cooling the cheesecake gradually also helps prevent cracks.

Can I freeze this cheesecake?
Yes. Wrap individual slices or the whole cheesecake tightly and freeze for up to 2 months. Thaw overnight in the refrigerator before serving.

Can I make it ahead of time?
Absolutely. This cheesecake is even better after chilling overnight, making it an ideal make-ahead dessert.

What can I serve with it?
It pairs wonderfully with whipped cream, vanilla ice cream, toasted coconut, fresh berries, or a drizzle of caramel sauce.

Servings & Nutrition

Servings: 10–12 slices

Prep Time: 25 minutes

Bake Time: 65 minutes

Cooling Time: 7 hours

Total Time: Approximately 8 hours 30 minutes

Approximate Nutrition (Per Serving)

• Calories: 485
• Protein: 8 g
• Carbohydrates: 41 g
• Fat: 33 g
• Saturated Fat: 19 g
• Cholesterol: 125 mg
• Fiber: 1 g
• Sugar: 31 g
• Sodium: 290 mg

This Pineapple Upside-Down Cheesecake combines the rich creaminess of classic cheesecake with the sweet tropical flavors of caramelized pineapple and cherries. The buttery graham cracker crust, silky filling, and glossy fruit topping create a dessert that’s both elegant and comforting. Whether you’re celebrating a special occasion or simply treating yourself, this show-stopping cheesecake is guaranteed to impress with every creamy, fruity, and irresistible bite.