Introduction

This Pineapple Upside-Down Cheesecake combines the classic tropical sweetness of pineapple and cherries with the creamy richness of cheesecake. It’s an impressive dessert that’s surprisingly easy to make and perfect for any occasion.

A slice of cheesecake with four visible layers sits on a white plate over a white marbled surface. The bottom layer is a crumbly brown crust. Above it is a thick, creamy off-white cheesecake layer with a smooth yet slightly airy texture. On top of this is a bright yellow pineapple glaze layer that is shiny and slightly translucent, with pineapple slices embedded inside. The top layer has several glossy, red cherries arranged in the center, with a swirl of white whipped cream positioned behind them. The lighting highlights the shiny fruits and creamy textures. photo taken with an iphone --ar 4:5 --v 7

Ingredients

1 1/2 cups graham cracker crumbs
1/4 cup unsalted butter, melted
1/2 cup brown sugar
6 to 8 pineapple rings, canned or fresh
6 to 8 maraschino cherries
24 ounces cream cheese, softened
3/4 cup granulated sugar
1/2 cup sour cream
1 teaspoon vanilla extract
3 large eggs

Instructions

Step 1: Preheat the oven to 325°F. Grease a springform pan and sprinkle the brown sugar evenly on the bottom. Arrange the pineapple rings on top and place a maraschino cherry in the center of each ring. Drizzle with melted butter.
Step 2: In a small bowl, combine graham cracker crumbs with melted butter. Press this mixture evenly over the pineapple and brown sugar layer. Freeze the pan for 10 to 15 minutes to set the crust.
Step 3: In a large bowl, beat the softened cream cheese and granulated sugar together until smooth and creamy. Add the eggs one at a time, mixing slowly after each addition to combine fully.
Step 4: Add the sour cream and vanilla extract to the cream cheese mixture. Mix until everything is fully combined and the batter is smooth.
Step 5: Pour the cheesecake filling over the crust and pineapple layer in the springform pan. Use a spatula to smooth the top evenly.
Step 6: Place the springform pan inside a larger baking pan and add hot water to create a water bath. Bake the cheesecake for 60 to 70 minutes, or until the center is mostly set but still slightly jiggly.
Step 7: Turn off the oven, crack the oven door open, and let the cheesecake cool gradually inside for 1 hour to prevent cracking.
Step 8: Refrigerate the cheesecake for at least 4 hours or preferably overnight to fully set.
Step 9: When ready to serve, run a knife around the edge of the pan, release the springform, and carefully invert the cheesecake onto a serving plate so the pineapple and cherry layer is on top.

Tips & Variations

Use fresh pineapple rings for a brighter flavor and firmer texture, or canned rings for convenience.
For extra moisture, brush the pineapple rings lightly with pineapple juice before assembling the layers.
If you prefer a gluten-free crust, substitute the graham cracker crumbs with crushed gluten-free cookies or nuts.
Adding a teaspoon of lemon zest to the cheesecake batter can add a refreshing citrus note.

Storage

Store the cheesecake covered in the refrigerator for up to 4 days. Keep it tightly wrapped or in an airtight container to prevent it from absorbing other fridge odors. Reheat is not recommended, but serving it slightly warmed is possible by letting it sit at room temperature for 15 minutes.

How to Serve

A close-up view of a slice of cheesecake with three distinct layers: the bottom layer is a crumbly brown crust, the middle layer is a thick, creamy white cheesecake with a smooth texture, and the top layer is a shiny, yellow pineapple glaze with visible pineapple slices. On top of the pineapple layer, there are several bright red cherries and a swirl of white whipped cream placed toward the back. The slice is served on a white plate, with a soft blurred background and a white marbled surface underneath. Photo taken with an iphone --ar 4:5 --v 7

Serve this delicious recipe with your favorite sides.

FAQs

Can I use fresh pineapple instead of canned?

Yes, fresh pineapple rings work beautifully and offer a fresh, juicy flavor. Be sure to pat them dry to avoid excess moisture that could affect the crust.

How do I prevent cracks in the cheesecake?

Gradual cooling in the oven with the door slightly open helps prevent cracks. Also, using a water bath during baking provides gentle, even heat that reduces the chance of cracking.