Previous research has highlighted the value of technology to enhance learning. However, digital inclusion research has argued that many issues such as skills, access, usability and choice impact on the effectiveness of technology to enhance learning. The findings in this paper add to the debate by highlighting the importance of value and context. In particular, the value that institutions and individuals place on the role of further and higher distance learning in a prison can affect technology-enhanced learning in that context. This research identified that despite good IT skills and improved technologies, prison learners’ access and use of technology is hampered by conflicting priorities amongst the multiple organisations controlling prisoner activities. This can lead to a prison in which menial work is valued far higher than learning. Technology-enhanced distance learning, perceived by many to be a lifeline in a desolate environment, is heavily restricted in such prisons. The situation is thought to be deteriorating as the number of organisations involved increases and the Government's plans for “working” prisons gather pace.