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Tropical Pineapple Upside Down Cheesecake with Caramel Glaze

A silky vanilla cheesecake baked over a caramelized brown sugar pineapple layer, flipped at serving to reveal a glossy, tropical topping.
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Prep Time 25 minutes
Cook Time 1 hour 5 minutes
Cooling and Chilling Time 8 hours
Total Time 9 hours 30 minutes
Servings: 12 people/slices
Calories: 390
Ingredients Equipment Method

Ingredients
  

4 tbsp melted butter, 2/3 cup brown sugar, 7 to 8 pineapple rings (drained and dried), 7 to 8 maraschino cherries (pineapple layer)
1 and 1/2 cups graham cracker crumbs, 3 tbsp sugar, 1/3 cup melted butter (crust)
3 x 8oz cream cheese (room temp), 1 cup sugar, 3 eggs, 1/2 cup sour cream, 1/4 cup pineapple juice, 1 tsp vanilla, 2 tbsp flour (filling)

Equipment

  • 1  9-inch springform pan
  • 1 large mixing bowl
  • 1 hand mixer or stand mixer
  • 1 small saucepan
  • 1 roasting pan for water bath
  • 1 heavy-duty aluminum foil
  • 1 large flat serving plate or cake board

Method
 

Preheat oven to 325 degrees F. Line pan base with parchment, grease sides, double-wrap in foil.
    Layer melted butter and brown sugar in pan base. Arrange pineapple rings over sugar. Place cherry in each ring center.
      Mix graham crust ingredients and set aside.
        Beat cream cheese until smooth. Add sugar, flour, then eggs one at a time on low. Fold in sour cream, pineapple juice, vanilla.
          Pour filling gently over pineapple layer. Press graham crust mixture firmly over the top of the filling.
            Bake in water bath 60 to 65 minutes until edges set, center wobbles. Cool in oven 1 hour. Refrigerate 8 hours or overnight.
              Run knife around edge, place serving plate on top, flip in one smooth motion. Peel parchment. Serve cold.