This chapter examines lessons learnt from a study of the use of e-learning within the rail sector in Australia and explores factors that inhibit or advance its organisational effectiveness. We examine the social, organisational and technical influences on the way employees perceive and use e-learning. By examining these issues, we aim to demonstrate that successful organisational adoption of e-learning is influenced by factors beyond the systems themselves and requires a more holistic understanding of the target workforce and the suitability of the e-learning tasks. Without a clear understanding of these relationships, organisations run the real risk of investing heavily in e-learning without receiving benefits, or worse still, negatively impacting their ability to deliver training.