Presented by Cheryl Dobbs at the BDA International Conference 2014. As part of a qualitative study that investigated the different contexts in which students used digital technologies to support their personal difficulties with writing, this paper focuses upon one student's experience. It culminated in an exploration of his use of different technologies and specifically his adoption of speech recognition software to support his issues with dyslexia and dyspraxia. This student’s experience does not dwell purely upon successful implementation but demonstrates the problems, frustrations and barriers he encountered as he endeavoured to strive for productivity in different educational environments. This included his experience in both primary and secondary schools, and subsequently university. Some of the strategies he ultimately employed to facilitate use will be explored, since these emphasise the importance of personal autonomy and responsibility for his own learning needs.