In a mixing bowl, combine the softened cream cheese and powdered sugar. Use an electric mixer to beat them together until smooth and creamy, about 2-3 minutes. This ensures there are no lumps in the filling.

Add the drained crushed pineapple and vanilla extract to the cream cheese mixture. Stir gently with a spatula until fully incorporated. The pineapple adds sweetness and moisture to the filling.

In another bowl, whip the chilled heavy cream until stiff peaks form, about 3-5 minutes. This will give the filling a light and airy texture.

Gently fold the whipped cream into the pineapple mixture, being careful not to deflate the whipped cream. This step is crucial for maintaining the lightness of the filling.

In a separate bowl, combine the graham cracker crumbs and melted butter. Mix until the crumbs are evenly coated with butter, resembling wet sand.

Spread half of the graham cracker mixture evenly in the bottom of a 9x13 inch baking dish. This will form the base layer of the cake.

Spoon half of the pineapple filling over the graham cracker layer and spread it evenly with a spatula.

Repeat the layers: add the remaining graham cracker mixture, followed by the rest of the pineapple filling. Smooth the top with a spatula.

Cover the dish with plastic wrap and refrigerate for at least 4 hours, or overnight if possible. This allows the graham crackers to soften and the flavors to meld.

Once chilled, remove the cake from the refrigerator. If desired, sprinkle sweetened shredded coconut and chopped pecans on top for added texture and flavor.

Cut into squares and serve chilled. Enjoy the refreshing taste of pineapple in every bite!