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Pineapple Upside-Down Cheesecake

Creamy cheesecake meets caramelized pineapple in this stunning upside-down dessert. Perfect for parties, holidays, and tropical-inspired celebrations.
Prep Time 25 minutes
Cook Time 1 hour 10 minutes
Total Time 1 hour 35 minutes
Course Dessert
Cuisine American
Servings 12
Calories 410 kcal

Ingredients
  

For the Pineapple Topping

  • ½ cup brown sugar
  • 6-8 pineapple rings (canned or fresh)
  • 6-8 maraschino cherries
  • ¼ cup unsalted butter, melted

For the Crust

  • 1 ½ cups graham cracker crumbs
  • ¼ cup unsalted butter, melted

For the Cheesecake Filling

  • 24 oz cream cheese, softened
  • ¾ cup granulated sugar
  • 3 large eggs
  • ½ cup sour cream
  • 1 tsp vanilla extract

Instructions
 

1. Prepare the Pineapple Layer

  • Preheat the oven to 325°F (163°C).
  • Grease a springform pan.
  • Sprinkle brown sugar evenly over the bottom.
  • Arrange pineapple rings in a single layer and place a cherry in each center.
  • Drizzle melted butter over the fruit.

2. Make the Crust

  • Mix graham cracker crumbs with melted butter.
  • Press the mixture gently over the pineapple layer.
  • Freeze for 10–15 minutes to help it firm up.

3. Prepare the Cheesecake Filling

  • Beat cream cheese and sugar until smooth.
  • Add eggs one at a time, mixing slowly.
  • Add sour cream and vanilla; mix until creamy and combined.

4. Assemble the Cheesecake

  • Pour the cheesecake filling over the chilled crust and pineapple layer.
  • Smooth the top with a spatula.

5. Bake

  • Place the springform pan in a water bath.
  • Bake for 60–70 minutes, until the center is almost set but slightly jiggly.

6. Cool and Chill

  • Turn off the oven, crack the door, and let it cool for 1 hour.
  • Refrigerate for at least 4 hours or overnight.

7. Invert and Serve

  • Run a knife around the edge.
  • Release the springform pan.
  • Carefully invert the cake onto a serving plate to reveal the caramelized pineapple topping.

Notes

  • For the cleanest slices, chill overnight before serving.
  • Canned pineapple produces the most consistent results.
  • Always invert carefully to keep the fruit layer intact.