In the first semester of 1997, once again, we taught our introductory Database Management (CS230) course to around 350 students on our two main campuses. On this occasion, we used the e-mail, NewsGroups, Telnet and the World Wide Web capabilities extensively to support access to teaching and learning materials, for promulgation and submission of assignments and for staff-staff-student-student communication. In this context, students encountered challenging difficulties arising out of what might be described as ‘problems with socio-technical systems’. This paper describes the several elements of the teaching programme the curriculum elements, the teaching staff and the technology intended to support each of these. With most of these elements, we encountered a number of ‘small’ problems. Taken in conjunction, these several difficulties presented students with considerable impediments to successful learning in this subject. The paper concludes with observations concerning conditions which must be in place for Internet-augmented teaching and learning to be successful and enjoyable and reports some performance data which indicate a positive—although not strong—benefit from the use of the WebTests upon the final examination results. We include a ‘pre-fiight checklist’ for each element in the programme and each linkage between them. The prediction is that the need for checklists of this kind will increase as we increase the number and remoteness of links in the teaching chain, the number and experience of sources of communication contained in those links and increasingly challenge the technical reliability of the linkages, and as each of those multi-faceted links is subject to rapid evolution.