Step 1: Combine sugar and cornstarch in a saucepan. Stir in pineapple, including juice (except reserve 2 tbsp juice for whipped cream), and water.
Step 2: Cook over medium-high heat, stir constantly until mixture thickens and come to a boil, about 10 minutes. Allow to boil for 1 1/2 minutes, then remove from heat.
Step 3: Stir in vanilla extract and set aside to cool for about 10 minutes.
Step 4: Meanwhile, beat cream cheese, sugar, coconut extract and coconut rum together in a medium sized bowl until smooth. Stir in whipped cream. Pour filling into cooled pie crust and smooth into an even layer.
Step 5: Top cream cheese mixture with pineapple mixture. Spread into an even layer.
Step 6: Refrigerate until firm.
Step 7: Whip heavy whipping cream until it begins to thicken. Add powdered sugar, reserved 2 tablespoons of the pineapple juice and coconut extract and whip until stiff peaks form.
Step 8: Spread whipped cream on the top of the pie. Garnish top with pineapple slices, toasted coconut and cherries. Chill until ready to serve
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