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Pineapple Upside Down Cheesecake Recipe

Combine the tropical charm of pineapple with the creamy decadence of cheesecake in this showstopping Pineapple Upside-Down Cheesecake. A layer of caramelized pineapple and cherries sits atop a rich, velvety cheesecake with a buttery graham cracker crust. Perfect for celebrations or simply indulging your sweet tooth!
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Course: Dessert
Cuisine: American
Prep Time: 25 minutes
Cook Time: 1 hour 20 minutes
Chilling Time: 8 hours
Total Time: 9 hours 45 minutes
Calories: 804kcal
Author: Anne Carter
Servings: 10

Equipment

Ingredients

Pineapple Compote

  • 6 cups pineapple rings quartered, with juice drained & reserved This equates to 3 cans of pineapple rings 1074 grams of pineapple
  • 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 276 grams
  • 1/2 cup salted butter melted 113 grams
  • 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 This is available in the baking aisle of most grocery stores
  • 1 cup heavy whipping cream
  • 1/4 cup + 2 tbsp powdered sugar
  • 2 tsp vanilla extract

For Decorating:

  • maraschino cherries

Instructions

  • Make Pineapple Filling: Cook pineapple, brown sugar, and juice until syrupy, then thicken with cornstarch slurry. Cool completely.
    cool-pineapple-filling-for-cheesecake
  • Prepare Crust: Preheat oven to 350°F, mix graham crumbs with melted butter, press into a springform pan, and bake for 10 minutes.
    make-cheesecake-filling-with-pineapple
  • Make Cheesecake Filling: Beat cream cheese and sugar, add eggs one at a time, then mix in vanilla, sour cream, and optional rum.
    assemble-pineapple-cheesecake-layers.j
  • Set Up Water Bath: Boil water and place the springform pan inside a 10-inch pan, then both inside a roasting pan.
  • Assemble Cheesecake: Layer half the cheesecake batter, pineapple filling, and remaining batter in the crust.
    cool-pineapple-cheesecake-in-oven
  • Bake Cheesecake: Bake in the water bath for 1 hour 25 minutes to 1 hour 45 minutes, then cool in the oven for 1 hour.
    bake pineapple cheesecake
  • Chill Cheesecake: Refrigerate for at least 6 hours or overnight.
  • Make Stabilized Whipped Cream: Beat cream with sugar and vanilla, adding liquified gelatin until stiff peaks form.
  • Serve: Top cheesecake with pineapple, pipe whipped cream, garnish with cherries, and enjoy!
    make-stabilized-whipped-cream-for-cheesecake

Nutrition

Calories: 804kcal | Carbohydrates: 86g | Protein: 10g | Fat: 47g | Saturated Fat: 27g | Polyunsaturated Fat: 2g | Monounsaturated Fat: 13g | Trans Fat: 0.3g | Cholesterol: 190mg | Sodium: 498mg | Potassium: 434mg | Fiber: 2g | Sugar: 68g | Vitamin A: 1783IU | Vitamin C: 14mg | Calcium: 187mg | Iron: 2mg