The Systems Group at the Open University has always seen diagramming as an essential skill for students to learn and use properly if they are to become effective systems practitioners. However, teaching students at a distance to use diagramming effectively has posed challenges to both Lecturers and Students alike. While we have tried to provide some face-to-face opportunities to help teach this skill we have had to rely heavily on technological means most of the time. This paper reviews the role of diagramming in systems studies generally and specifically in Open University courses and assesses the advantages and disadvantages of the various technological methods used to teach diagramming over 30 years by the Systems Group. In so doing we try to determine how much the technology hinders or helps budding systems practitioners.