This chapter examines the implementation of two learning management systems (LMS) in a university environment. Within the context of a case study and from the perspective of academic users, there is a review of the technological and organizational challenges that arise. There is an in-depth analysis of the implementation in terms of what went well and what should be done differently (i.e., lessons learned). Along with the macro-environmental factors that influence the global e-learning space, the related pedagogical issues, learning models, and technological toolsets are also explored. The authors hope that the experiences chronicled in the case study may act as a lesson to others contemplating such a project of the many technical and organizational issues that need to be addressed, with an emphasis on understanding the importance of the viewpoint of academic users.