Wash and dry the strawberries. Using a sharp knife, cut off the top of the strawberry where the red transitions into white. Trim the bottom of the strawberry so it can stand on its own. Tilt the knife slightly and trace along the white line on the inside of the strawberry to hull it.
In a small bowl, combine the cream cheese, powdered sugar, and vanilla. Mix well until smooth and creamy.
Transfer the cream cheese mixture into a piping baggie and pipe enough of the mixture into each strawberry's cavity to overfill it.
If you're not serving the strawberries immediately, let them chill in the refrigerator to allow the flavors to meld together and the filling to set.
Just before serving, dip the top of each cream cheese-filled strawberry into the crushed graham crackers. Serve and enjoy!