Increasingly the demanding nature of Attention Deficit Hyperactivity Disorder (ADHD) is being acknowledged as having a lifelong impact. This paper reflects upon two specific areas of communication difficulty often associated with ADHD, which are pragmatic language and dysfluency. Pragmatic language refers to the service user’s ability to use appropriate and applicable language. Dysfluency refers not only to a stammer, but difficulties with timing and maintaining a conversational flow. The latter is often hindered by the poor use of pragmatic skills. A small-scale qualitative research study was carried out in a Community Rehabilitation Company (CRC), to explore what support and understanding of ADHD was held by CRC staff and service users with ADHD. One to one semi- structured interviews were carried out with thirteen CRC staff and six service users. The research questions did not specifically target pragmatic and dysfluent language, yet both emerged from the data collection, indicating a relevance to communication style and ability when carrying out probation work. The research highlighted that CRC staff were not always suitably resourced to deal with ADHD service users. Access to suitable training were lacking, and instances of loss of experienced staff were commonplace. Despite the best efforts of the CRC staff, evidence suggested that overall there was poor understanding of ADHD and failure to identify needs. However, there was some evidence of good practice which supported pragmatic language and dysfluent challenges for ADHD service users. As recognition of a more neurodiverse population increases, accommodation within a unified probation services becomes a pressing issue.