Since the introduction of chat technology there has been resistance within education to fully engage with it partly due to policy making that has left teachers disempowered (UCLAN 2002:66). Unlike other innovative technologies, its use has been limited. Pastoral support has developed significantly in education but in some instances, like chat rooms, has been viewed with scepticism. One reason for this scepticism may be that a clear measurable link between support and achievement is not easily proven. However, there is widespread acceptance that academic success is not the only measure of intelligence (Gardner 2006) and that supporting and understanding how young people communicate with each other and feel supported is an important research area for development. This research uses exploratory case study to consider the introduction of a bounded bespoke chat system into a sixth-form college. A range of sources are considered including semi-participant observation, chat transcripts and observational diaries. It is shown that the introduction of such a system can be managed effectively and be useful for students. The research reveals there are critical drivers for its successful introduction. The first relates to the role of the moderator, including perceptions about them and their impact on rules and boundaries for behaviour. The study shows that finding moderators with the appropriate level of skill is challenging. It also shows that students access support online in different ways compared to offline and that the use of topics can influence their behaviour. Anonymity, gender, the use of „text speak‟ and participant consciousness all affect communication. Future research is proposed into the specific impact of the gender of the moderator on chat usage, the impact of an individual institutional culture on the willingness of learners to use chat, attitudes of stakeholders towards chat and the purpose of "lurking" in bounded environments.