Heat the oven to 300 °F, melt the butter for the crust in the microwave, let it cool, then mix it with the graham crumbs until every crumb looks evenly moistened. The mixture should look like damp sand and clump lightly when pressed in your hand.

Press 2 cups of the crumb mixture firmly into a 9x9 square pan and bake for 8 to 10 minutes, then set the pan on a wire rack to cool completely. By the end, the crust should look lightly golden and smell buttery and toasted, not dark at the edges.

Beat the softened cream cheese and softened butter together until fully smooth, then add the sifted powdered sugar on low, 1 cup at a time, before beating again until fluffy. The mixture should look pale, even, and creamy with no streaks or little lumps before you move on.

Fold 1 heaping tablespoon of the well-drained pineapple into the cream cheese mixture with a rubber spatula, then spread that layer over the cooled crust. The filling should glide across the crust in a thick, even layer instead of sliding or pooling.

Fold the remaining drained pineapple into the Cool Whip, spread it over the cream cheese layer, and finish with the remaining 1/2 cup graham crumb mixture on top. The top layer should stay airy and uniform, with the pineapple evenly distributed instead of settling into wet pockets.

Refrigerate the dessert for at least 4 hours before slicing. When it’s ready, the layers should feel cold and set, and a knife should pass through with clean edges instead of dragging.