Mix the crushed cookies, sugar, and melted butter until a moist crumbly mixture forms. Ensure every crumb is coated in butter so the base firms up evenly once chilled. The texture should resemble damp sand and hold together lightly when pressed.
Press this base into the bottom of a baking dish and refrigerate. Spread it evenly and press gently without compacting it too firmly, which keeps the crust tender rather than overly hard. Chilling helps the butter solidify and stabilizes the base before adding the creamy filling.
In a bowl, beat the cream cheese with the powdered sugar until creamy. The cream cheese should be fully at room temperature to blend smoothly without lumps. Beat until the mixture looks pale, velvety, and easily spreadable.
Add the whipped cream and mix gently. Fold it in using slow, sweeping motions to keep the mixture light and airy. Avoid vigorous stirring, which can deflate the whipped cream and reduce the cheesecake’s soft texture.
Add the well-drained pineapple and incorporate. Patting the pineapple dry or letting it drain thoroughly prevents excess moisture from thinning the filling. Fold it evenly to distribute the fruit throughout.
Spread the cream over the base and refrigerate for 3 to 4 hours, or until firm. The mixture will gradually set into a stable, sliceable texture. Longer chilling—such as overnight—enhances the flavor and creates cleaner cuts.
Decorate with extra pineapple pieces and serve chilled. Adding fresh or reserved pineapple just before serving enhances presentation and highlights the dessert’s fruity character.
