This dissertation presents three studies conducted at Monash University, Australia using qualitative case study methods to investigate technology adoption from three perspectives - teaching academics, educational designers and students. The main study explores technology adoption by teaching academics and found a range of facilitating and impeding factors that influence adoption. Contextual factors such as power and politics of the institution, organisational infrastructures and policy frameworks were also found to shape adoption. Of the two smaller studies, one analyses the readiness of learners to use web-based technologies for learning, and the other examines the expansion of educational designers'' roles due to technology adoption. The three studies in the dissertation found that the institution, its people, structures and processes must all adapt, evolve and grow in order to provide effective, engaging, student-centred web-based learning environments. Students in turn must be enabled to manage their study, make use of the technologies and maximise their learning experience.