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Close-up shot of the cheesecake on a serving platter, topped with pineapple filling, a generous swirl of whipped cream, and garnished with maraschino cherries.

Pineapple Upside down Cheesecake Recipe

This Pineapple Upside Down Cheesecake combines the classic flavors of a sweet, caramelized pineapple topping with a rich, creamy cheesecake base. It’s a delightful twist on the traditional, with a perfect balance of tangy and sweet in every bite. A showstopper for any occasion!
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Prep Time 1 hour
Cook Time 1 hour 45 minutes
Total Time 2 hours 45 minutes
Course Dessert
Cuisine American
Servings 12
Calories 804 kcal

Equipment

  • 9-inch springform pan
  • Mixing bowls
  • Electric mixer
  • Whisk
  • Spatula
  • Knife for slicing pineapple
  • Measuring cups and spoons
  • Small saucepan

Ingredients
  

Pineapple Compote

  • 6 cups pineapple rings quartered
  • 1 and 1/4 cups pineapple juice
  • 2/3 cup + 1 tbsp dark brown sugar packed 300 grams
  • 2 tbsp + 1 tsp corn starch
  • 2 tbsp + 1 tsp water
  • 2 tsp vanilla extract
  • 2-3 tbsp vanilla rum or coconut rum optional

For the Crust:

  • 3 cups graham cracker crumbs
  • 1/2 cup salted butter melted

For the Cheesecake Batter

  • 32 ounces full fat cream cheese softened at room temperature 906 grams
  • 1 and 1/2 cups brown sugar 330 grams
  • 4 large eggs at room temperature
  • 3/4 cup full fat sour cream at room temperature 180 grams
  • 2 tsp vanilla extract

For the Whipped Cream

  • 4 tsp cold water
  • 1 tsp plain powdered gelatin
  • 1 cup heavy whipping cream
  • 1/4 cup + 2 tbsp powdered sugar
  • 2 tsp vanilla extract

For Decorating:

  • maraschino cherries

Instructions
 

  • Make Pineapple Filling/Topping: Stir cornstarch and water until dissolved. In a saucepan, cook pineapple chunks, brown sugar, and pineapple juice over high heat for 18-25 minutes until liquid reduces to a syrupy consistency. Add cornstarch slurry and cook for 1-2 minutes until thickened. Stir in vanilla and rum, then cool in the fridge.
    Close-up shot of a saucepan on the stove, with pineapple chunks, brown sugar, and pineapple juice simmering together to create a syrupy consistency, with cornstarch slurry being added.
  • Make Crust: Preheat oven to 350°F. Spray a 9-inch springform pan and line the bottom with parchment paper. Mix melted butter with graham crumbs and press into the pan. Bake for 10 minutes and set aside.
    Close-up shot of a 9-inch springform pan lined with parchment paper, with graham cracker crumbs mixed with melted butter pressed into the bottom, ready to be baked.
  • Make Cheesecake Filling: Beat softened cream cheese with sugar until creamy. Add eggs one at a time, then mix in vanilla, sour cream, and rum. Stir until smooth.
    Close-up shot of a large mixing bowl, with softened cream cheese being beaten with brown sugar until creamy, followed by eggs, sour cream, vanilla, and rum being stirred in.
  • Prepare Water Bath: Boil water in a large pot. Place the springform pan inside a 10-inch cake pan, then set in a roasting pan. Pour boiling water into the roasting pan until it reaches 2 inches deep.
    Close-up shot of a roasting pan with a 10-inch cake pan holding a springform pan inside, with boiling water poured into the roasting pan to create a water bath for the cheesecake
  • Assemble Cheesecake: Pour half the cheesecake batter into the pan. Add 1/3 of the pineapple filling. Pour the remaining batter on top and smooth out.
  • Bake Cheesecake: Bake at 350°F for 1 hour 25 minutes to 1 hour 45 minutes. The center should have a slight wobble, and the knife should come out clean from the edge. Let cool in the oven for 1 hour.
    Close-up shot of a cheesecake baking in the oven, with the center slightly wobbling, indicating it is ready to come out after baking for 1 hour and 25 minutes to 1 hour 45 minutes
  • Cool Cheesecake: Remove from the oven and let cool to room temperature. Refrigerate for at least 6 hours or up to 1 day.
  • Make Whipped Cream: Dissolve gelatin in water and microwave for 5 seconds. Beat whipped cream ingredients, then add gelatin mixture. Beat until stiff peaks form.
    Close-up shot of a bowl with whipped cream ingredients being beaten, with a small bowl of dissolved gelatin mixture ready to be added to the whipped cream for stiff peaks.
  • Serve Cheesecake: Remove the cheesecake from the springform pan. Top with pineapple topping and whipped cream. Garnish with maraschino cherries.
    Close-up shot of the cheesecake on a serving platter, topped with pineapple filling, a generous swirl of whipped cream, and garnished with maraschino cherries.
  • Store Leftovers: Store leftovers in an airtight container in the fridge for 3-4 days.