In a medium mixing bowl, combine graham cracker crumbs with melted butter until evenly coated. Press the mixture into the bottom of an 8x8 or 9x9-inch dish to form a solid crust. Chill for about 15 minutes.

In a large bowl, beat cream cheese and 1 cup of powdered sugar until creamy and free of lumps, about 2-3 minutes. Whip heavy cream with remaining powdered sugar and vanilla extract until stiff peaks form. Fold the whipped cream into the cream cheese mixture gently.

Gently fold in the well-drained crushed pineapple until just combined.

Spread the pineapple filling over the chilled graham cracker crust evenly. Optionally, sprinkle some extra graham cracker crumbs on top.

Cover with plastic wrap or foil and refrigerate for at least 4 hours or overnight. This ensures the best flavor and texture.

Cut into squares for serving. Serve cold, optionally garnished with pineapple chunks or a dollop of whipped cream.