This chapter sets much of the theoretical framework for the questions addressed through the empirical work reported in Chapters 4-6 of this book (further theoretical questions concerning the role of proportionality are considered in Chapter 4). Two theories of punishment in which communication performs a central role form the main subject matter of the present chapter: the theories put forward by von Hirsch (1993) and Duff (2001). Before discussing these theories and their possible application to community penalties, the chapter ﬁrst considers the contemporary context against which community penalties are delivered. In doing so, I make the case for a stronger conceptual framework for sanctions that are non-custodial but still personally restrictive. My central argument is that community-based interventions have fared badly in a comparison with custody and that the provisions for mixed custodycommunity disposals in the recently enacted Criminal Justice Act 2003 do not improve their future prospects.