Prepare the crust mixture: In a medium mixing bowl, combine the graham cracker crumbs and granulated sugar. Pour the melted butter over the dry ingredients and stir until all crumbs are evenly coated. The mixture should resemble damp sand.

Press the crust: Transfer the crumb mixture into an 8×8-inch baking dish. Spread evenly and press firmly into the bottom of the dish using the bottom of a flat measuring cup or sturdy glass. Refrigerate while preparing the filling.

Drain the pineapple: Place the crushed pineapple in a fine-mesh strainer and press with the back of a spoon to remove as much juice as possible. Set aside.

Whip the cream cheese base: Beat the softened cream cheese with a hand-held electric mixer on medium speed for about two minutes until creamy and smooth. Add the powdered sugar and beat for another minute until fully combined and lump-free.

Incorporate the pineapple and whipped topping: Fold the drained crushed pineapple into the cream cheese mixture. Add the thawed whipped topping and gently fold until fully combined and no white streaks remain.

Assemble the dessert: Remove the chilled crust from the refrigerator. Spread the pineapple filling evenly over the crust and smooth the top.

Chill thoroughly: Cover the baking dish and refrigerate for at least four hours, preferably overnight, until the dessert is firm and slices hold their shape.