Community-based further education in Scotland as a context for teaching and learning plays a considerable role in implementing the widening participation to learning opportunities strategies that have become increasingly important aspects of the policy agenda over a number of years (Gallacher et al. 2002). We have undertaken research designed to explore the distinctive aspects of these community learning contexts. In this chapter, we focus on the roles of staff, both teaching and core staff, in helping to create the distinctive learning cultures found within these centres. We argue that staff working in these centres have complex roles and face signiﬁcant challenges in undertaking these and suggest, as do other contributors to this book, that they need to understand learners’ lives outside the speciﬁc learning context under investigation. We focus on the importance of the learning relationships formed within and outwith the centres, and use the concepts of emotion work, underground working, and habitus to deepen our understanding of these relationships.