This paper describes research on a case of the introduction, into a large educational institution, of a complex timetabling system that was already well established in other similar organisations. The research has used a grounded theory approach to reveal details within complex phenomena in an organisation when a substantial new system was implemented. The study revealed three critical issues: Knowledge Transfer, System Capability, and Organisational Context that appeared to be related to the problems of implementing the new information system in the organisation. This research adds to the understanding of a common situation where management have an over simplified view of organisational work and assume that implementing a new computer based system can quite easily improve the performance of the organisation.