Some organisations appear to be more successful than others at adopting and implementing Knowledge Management (KM) systems. In this paper, the authors investigate why this situation may occur through a case study analysis of two organisations that have implemented KM systems. In the first case, the authors consider why one supposedly technologically literate organisation experienced problems implementing what could be termed a ‘tried and tested’ technical solution. In the second, the authors consider a supposedly technologically illiterate organisation’s more positive experiences with a ‘state of the art’ application. The focus of the analysis is on the interplay amongst the organisational factors that inhibited and facilitated the KM projects. Our case analysis suggests that a key factor is the levels of encouragement/discouragement for the use of the system that occur and their source: the technology, the organisation or both.