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Pineapple Upside-Down Cheesecake Recipe

5 Stars 4 Stars 3 Stars 2 Stars 1 Star 4.2 from 63 reviews
  • Author: Aiko
  • Prep Time: 30 minutes
  • Cook Time: 1 hour 10 minutes
  • Total Time: 5 hours 40 minutes
  • Yield: 12 servings
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Description

This Pineapple Upside-Down Cheesecake combines the classic tropical flavors of pineapple and cherries with a creamy, rich cheesecake layered on a buttery graham cracker crust. The caramelized pineapple topping adds a beautiful, glossy finish, making this dessert perfect for gatherings and special occasions.


Ingredients

Scale

Pineapple Topping

  • 1/2 cup packed brown sugar
  • 1/4 cup unsalted butter
  • 10–12 pineapple rings (canned or fresh)
  • Maraschino cherries (one for each ring)

Crust

  • 1 1/2 cups graham cracker crumbs
  • 1/4 cup granulated sugar
  • 6 tablespoons melted butter

Cheesecake Filling

  • 3 (8 oz) blocks cream cheese, softened
  • 1 cup granulated sugar
  • 1/2 cup sour cream
  • 1 teaspoon vanilla extract
  • 3 large eggs
  • 1/2 cup crushed pineapple (drained well)


Instructions

  1. Prepare the pineapple topping: In a small saucepan, melt the unsalted butter with the packed brown sugar over medium heat until the mixture starts to bubble and becomes caramel-like. Pour this caramel mixture into the bottom of a greased 9-inch springform pan. Arrange pineapple rings neatly over the caramel and place a maraschino cherry in the center of each pineapple ring. Set aside to let the topping settle.
  2. Make the crust: In a medium bowl, combine the graham cracker crumbs, granulated sugar, and melted butter. Mix until all crumbs are evenly coated and moist. Press this crumb mixture evenly on top of the pineapple rings in the springform pan, pressing slightly up the sides to form a firm crust. Place the pan in the refrigerator while you prepare the cheesecake filling to allow the crust to set.
  3. Preheat oven: Preheat your oven to 325°F (160°C). To prevent leaking during baking, wrap the outside of the springform pan with aluminum foil tightly. Prepare a larger baking dish or roasting pan for a water bath by filling it partially with hot water.
  4. Make the cheesecake filling: In a large mixing bowl, beat the softened cream cheese with the granulated sugar until the mixture is smooth and creamy. Add the sour cream and vanilla extract and mix well to incorporate. Add the eggs one at a time, beating just until combined after each addition to avoid overmixing. Gently fold in the well-drained crushed pineapple to the batter.
  5. Assemble and bake: Pour the prepared cheesecake filling over the chilled crust in the springform pan, spreading it evenly. Place the springform pan into the larger baking dish and carefully pour hot water into the outer pan until it reaches halfway up the side of the springform pan, creating a water bath. Bake the cheesecake in the preheated oven for 60 to 70 minutes, or until the center is just set but still slightly jiggly when shaken gently.
  6. Cool and chill: Carefully remove the cheesecake from the water bath and let it cool completely at room temperature. Once cooled, refrigerate the cheesecake for at least 4 hours or, preferably, overnight to ensure it is fully set and chilled.
  7. Flip and serve: To serve, run a knife gently around the edges of the cheesecake to loosen it from the pan. Place a serving platter over the pan and carefully invert the cheesecake, so the caramelized pineapples and cherries are now on top. Slice and enjoy this delicious pineapple upside-down cheesecake.

Notes

  • Make sure to fully drain the crushed pineapple to prevent excess moisture in the filling.
  • Wrapping the springform pan with foil is crucial to avoid water leakage during the water bath bake.
  • Use room temperature cream cheese to ensure a smooth, lump-free batter.
  • For best results, chill the cheesecake overnight to develop flavor and improve texture.
  • This cheesecake is best served chilled but can be kept refrigerated for up to 3 days.