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A slice of cheesecake on a plate, viewed from the side to show the texture of the layers.

Pineapple-Upside Down Cheesecake

  • Author: Lindsay
  • Prep Time: 45 Minutes
  • Cook Time: 2 Hours 5 Minutes
  • Total Time: 2 hours 50 minutes
  • Yield: 12 Slices
  • Category: Desserts
  • Method: Oven
  • Cuisine: American


This Pineapple Upside Down Cheesecake combines juicy baked pineapple in a brown sugar topping with a decadent cheesecake base.


For the Pineapple Layer

  • 7 tbsp butter, melted, divided
  • ½ cup packed brown sugar
  • 10 canned pineapple slices (reserve the juice)
  • 13 maraschino cherries
  • 1 cup graham cracker crumbs
  • 3 tbsp sugar
  • 3 tbsp butter

For the Cheesecake Layer

  • 24 oz cream cheese, room temperature
  • 1 cup light brown sugar, loosely packed
  • 3 tbsp all-purpose flour
  • ½ cup sour cream, room temperature
  • 6 tbsp pineapple juice, reserved from the can of pineapple rings
  • 2 tsp vanilla extract
  • 3 large eggs, room temperature


Make the Pineapple Layer

  1. Preheat the oven to 300°F. Line the bottom of a 9-inch springform pan with parchment paper, and grease the sides.
  2. Combine 4 tablespoons of melted butter with the brown sugar. Spread this evenly in the bottom of the pan.
  3. Pat the pineapple slices dry, so that you don’t add excess liquid to the topping. Arrange the pineapple slices and cherries over the brown sugar, and along the sides of the pan (see recipe post photos for guidance).
  4. Combine the graham cracker crumbs, sugar, and the remaining 3 tablespoons of butter. Spread this evenly on top of the pineapple slices, and gently press it into them.
  5. Prepare the pan for a water bath. Set the pan in the center of a large sheet of foil, and fold/crimp the sides of the foil up to the top edges of the pan. Set the pan aside.

Make the Cheesecake

  1. In a large bowl, beat the cream cheese, brown sugar, and flour on low speed, until well-combined and smooth. (Be sure to use a low speed to reduce the amount of air added to the batter. Air in the batter can cause cracks. Scrape down the sides of the bowl as you go.)
  2. Add the sour cream, pineapple juice, and vanilla to the mixture. Mix on low speed until well-combined.
  3. Add the eggs one at a time, mixing slowly to combine after each addition. Scrape down the sides of the bowl as needed to make sure everything is well-combined. 
  4. Pour the cheesecake batter into the crust.
  5. Place the springform pan inside another larger pan. Fill the outside pan with enough warm water to go about halfway up the sides of the springform pan. The water should not go above the top edge of the foil, or it might seep into the cheesecake.
  6. Bake for 1 hour and 5 minutes. The center should be set, but still jiggly.
  7. Turn off the oven and leave the door closed for 30 minutes. The cheesecake will continue to cook, but it will also slowly begin to cool down.
  8. Crack the door of the oven for 30 minutes to allow the cheesecake to continue to cool slowly. This helps prevent cracking.
  9. Remove the cheesecake from the oven and water bath wrapping, and refrigerate until firm, 5 – 6 hours or overnight.
  10. To plate the cheesecake, remove the sides of the springform pan. Place a serving platter on top of the cheesecake (which will be the bottom) and carefully invert the cake. Remove the bottom of the pan, and carefully peel back the parchment paper. Refrigerate the cheesecake until ready to serve.

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