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Pineapple Upside-down cheesecakes recipe card with complete instructions

Pineapple Upside-down Cheesecakes: A Tropical Twist in Every Bite

Abby Martin
A showstopping, nostalgic dessert combining caramelized pineapple upside-down cake and creamy pineapple cheesecake, just like The Cheesecake Factory.
Prep Time 20 minutes
Cook Time 1 hour 35 minutes
Total Time 8 hours 15 minutes
Course Dessert
Cuisine American
Servings 1 cake
Calories 376 kcal

Ingredients
  

  • 16 ounces cream cheese room temperature
  • 1/2 cup granulated sugar
  • 2 large eggs
  • 1/2 cup sour cream
  • 2 tablespoons pineapple juice
  • 1 teaspoon vanilla bean paste
  • 1/2 cup unsalted butter melted (for topping)
  • 1 cup packed light brown sugar for topping
  • 14 slices canned or fresh pineapple rings
  • 14 maraschino cherries
  • 1 1/2 cups plus 3 tablespoons all-purpose flour sifted
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1/2 cup unsalted butter melted (for cake batter)
  • 3/4 cup light brown sugar packed
  • 1/4 cup granulated sugar
  • 1 large egg
  • 1/4 cup sour cream
  • 1/2 cup milk
  • 1/4 cup pineapple juice
  • 1 tablespoon vanilla bean paste

Instructions
 

  • 1. Preheat oven to 325°F. Grease a 9-inch springform pan and wrap it in heavy-duty foil. Set aside.
  • 2. In a large bowl, beat cream cheese and 1/2 cup granulated sugar until smooth.
  • 3. Mix in eggs one at a time, then add 1/2 cup sour cream, 2 tablespoons pineapple juice, and 1 teaspoon vanilla bean paste. Beat until smooth.
  • 4. Pour cheesecake batter into prepared pan. Place pan in a large roasting dish.
  • 5. Reduce oven to 300°F. Place roasting dish with cheesecake in oven and fill roasting pan with hot water halfway up the sides of springform pan.
  • 6. Bake cheesecake for 45 minutes. Turn off oven and leave cheesecake inside for 20 minutes.
  • 7. Remove cheesecake from oven and water bath. Cool to room temperature, cover, and refrigerate at least 8 hours.
  • 8. For the topping, divide 1/2 cup melted butter between two 9-inch cake pans. Sprinkle 1/2 cup brown sugar in each pan.
  • 9. Arrange 7 pineapple rings and 7 cherries in each pan over the sugar. Set aside.
  • 10. Preheat oven to 350°F. In a large bowl, whisk flour, baking powder, baking soda, and salt.
  • 11. In another bowl, whisk 1/2 cup melted butter, 3/4 cup brown sugar, and 1/4 cup granulated sugar until smooth.
  • 12. Whisk in 1 egg, 1/4 cup sour cream, milk, 1/4 cup pineapple juice, and 1 tablespoon vanilla.
  • 13. Add wet mixture to dry and stir until just combined.
  • 14. Divide batter evenly between the two prepared pans, spreading gently over fruit.
  • 15. Bake cakes for 25-30 minutes, until a toothpick comes out clean and tops are golden brown.
  • 16. Cool cakes in pans on a rack for 10 minutes.
  • 17. Carefully invert cakes: one onto a cutting board, one onto serving plate.
  • 18. Remove cheesecake from springform pan. Place cheesecake on first cake layer, then top with second cake layer.
  • 19. Chill assembled cake in refrigerator for several hours before serving. Garnish with whipped cream if desired.

Notes

Use room temperature ingredients for a smooth cheesecake.
Bake cheesecake in a water bath to prevent cracks and keep it creamy.
Mix cheesecake filling on low speed to avoid incorporating too much air.
Cool cheesecake completely before refrigerating to set properly.
Invert cakes gently to keep pineapple and cherries in place.
Chill assembled cake for best slicing and flavor.
Keyword cheesecake, copycat, copycat pineapple upside down cheesecake, pineapple, pineapple upside down cake, retro dessert, The Cheesecake Factory, Vegetarian