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Pineapple Upside-Down Cheesecake Recipe

4.6 from 117 reviews

This Pineapple Upside-Down Cheesecake combines the luscious creaminess of classic cheesecake with the tropical sweetness of caramelized pineapple rings and maraschino cherries, all atop a buttery graham cracker crust. Baked in a water bath to ensure smooth texture and crack-free finish, this dessert delivers a visually stunning and deliciously rich treat perfect for any occasion.

Ingredients

Scale

Crust and Topping

  • 1 1/2 cups graham cracker crumbs
  • 1/4 cup unsalted butter, melted (plus extra for drizzling)
  • 1/2 cup brown sugar
  • 6 to 8 pineapple rings, canned or fresh
  • 6 to 8 maraschino cherries

Cheesecake Filling

  • 24 ounces cream cheese, softened
  • 3/4 cup granulated sugar
  • 1/2 cup sour cream
  • 1 teaspoon vanilla extract
  • 3 large eggs

Instructions

  1. Prepare the Pan and Pineapple Layer: Preheat your oven to 325°F (163°C). Grease a springform pan thoroughly and evenly sprinkle the brown sugar across the bottom. Arrange the pineapple rings over the sugar, placing a maraschino cherry in the center of each pineapple ring. Drizzle the melted butter evenly over this layer to aid caramelization during baking.
  2. Make and Set the Crust: In a bowl, combine the graham cracker crumbs with 1/4 cup melted butter until the mixture feels like wet sand. Press this mixture firmly and evenly over the pineapple and brown sugar layer in the pan. Place the pan in the freezer for 10 to 15 minutes to set the crust before adding the filling.
  3. Beat the Cream Cheese and Sugar: In a large mixing bowl, beat the softened cream cheese with the granulated sugar until the mixture is completely smooth and creamy, making sure there are no lumps.
  4. Add Eggs, One at a Time: Add the eggs one at a time to the cream cheese mixture, blending each egg slowly on low speed to maintain a smooth texture and prevent air bubbles.
  5. Incorporate Sour Cream and Vanilla: Add the sour cream and vanilla extract to the batter, mixing until it becomes fully combined and silky smooth.
  6. Pour Filling and Smooth Top: Pour the cheesecake filling carefully over the prepared crust and pineapple layer in the springform pan. Use a spatula to smooth the surface evenly.
  7. Bake Cheesecake in a Water Bath: Place the springform pan in a larger baking dish, then pour hot water into the larger dish until it reaches halfway up the sides of the cheesecake pan. Bake in the preheated oven for 60 to 70 minutes, until the center is mostly set but still slightly jiggly.
  8. Cool Gradually: Turn off the oven, crack the oven door open, and allow the cheesecake to cool slowly inside the oven for 1 hour. This gentle cooling helps prevent cracking.
  9. Chill Thoroughly: Remove the cheesecake from the water bath, cover, and refrigerate for at least 4 hours or overnight to let it fully set and develop flavors.
  10. Unmold and Serve: Once chilled, run a knife carefully around the edges of the pan to loosen the cheesecake. Release the springform latch, and carefully invert the pan onto a serving plate so the pineapple upside-down topping is revealed beautifully.

Notes

  • Use canned pineapple for best caramelization and uniformly shaped slices.
  • Baking the cheesecake in a water bath is essential to avoid cracks and ensure even cooking.
  • Allow the cheesecake to chill overnight before flipping it upside down to keep the layers intact and make unmolding easier.

Keywords: pineapple upside-down cheesecake, pineapple cheesecake, caramelized pineapple dessert, springform pan cheesecake, tropical cheesecake, maraschino cherries dessert