Combine Ingredients: In a medium saucepan, combine the undrained crushed pineapple, granulated sugar, and cornstarch.
Cook Filling: Place over a medium heat and bring to a boil, once boiling, continue to cook for 2 minutes, stirring constantly. Remove from heat and stir in 1/2 teaspoon of the vanilla extract until well combined.
Cool Filling: Pour into a clean bowl. Place in the refrigerator for 20-30 minutes until it cools down completely, otherwise the whipped cream will curdle when you fold it in.
Whip Cream: In a separate medium bowl, whip the heavy cream with the remaining 1/2 teaspoon of vanilla extract on medium-high speed for 2 minutes or until stiff peaks form. Do not over-beat.
Transfer Pineapple Filling: Pour the cooled pineapple filling into a large mixing bowl.
Fold In: Gently fold the whipped cream into the pineapple filling until well combined.
Spread Filling: Spread the pineapple filling over the broken biscuits, smoothing the top with a spatula.
Chill to Set: Cover the dessert with plastic wrap or a lid if your baking dish has one, and refrigerate for at least 2 hours, or until fully set.
Optional Garnish: Garnish with additional fresh pineapple, sliced strawberries, fresh mint or a sprinkle of shredded coconut. Enjoy!