Background: Two previous single-case studies have reported that voice recognition software (VRS) can be a powerful tool for circumventing impaired writing in aphasia. However, these studies report mixed results regarding transfer of skills to functional tasks, such as emailing. Method: A single-case therapy study was conducted with "Stephen" a 63-year-old man with fluent aphasia and severe acquired dysgraphia and dyslexia limiting his social participation and ability to return to work. Treatment consisted of 16 one-hour sessions. Stephen was trained to use Dragon NaturallySpeaking (RTM) VRS to assist writing and Read+WriteGold (RTM) text-to-speech software to assist reading, and to develop computer skills required to use email. Outcome measures evaluated writing efficiency and communicative effectiveness, the functional impact of the intervention, and changes in participation. Results: Training produced significant gains in the efficiency and communicative effectiveness of Stephen's writing, despite his underlying writing impairment remaining unchanged. Gains generalised to everyday functional communication, leading to increased social participation with Stephen undertaking a wider range of social activities and increasing his social network following treatment. Gains were maintained at follow-up assessment. Discussion: Results indicate that a relatively short training period with assistive technologies achieved extensive generalisation to independent, functional communicative writing. Indeed, for this case, VRS training may have exceeded the degree of improvement in functional text writing that could have been achieved through impairment therapy, since gains were not limited to treated vocabulary. Some challenges were encountered in training Stephen to use VRS but, through adaptations to the training process, were largely overcome. Importantly, regaining independent writing skills resulted in profound and life-changing improvements to social participation. This may have resulted in Stephen reconnecting with important aspects of his pre-stroke identity, and improving his self-esteem. Conclusion: This case adds to a small evidence base indicating that training in the use of VRS, in combination with text-to-speech software, may be an effective way to address writing impairments in chronic aphasia for individuals with relatively well-preserved spoken output. Not only can these technologies improve the efficiency and communicative effectiveness of writing, they can also lead to significant gains in functional communication and social participation. Further research is needed trialling this approach with a larger group of people with aphasia.