While some research within the realms of oﬀender rehabilitation has been undertaken with regard to what is understood by therapeutic relationships, a number of tensions and issues emerge when a therapeutic relationship, in its purest form, is placed within a correctional context. Of course, the nature of this context is not only ﬂuid from moment by moment, but also varies from context to context. This presents many challenges. First, how one might capture such a context and, second, how such a context inﬂuences a therapeutic relationship and changes the way it is formed and nurtured. This chapter will examine what is understood by a therapeutic relationship, how a correctional context (such as prison or probation) may alter the construction and meaning of a therapeutic relationship and how oﬀenders and probation staﬀ see these relationships. Alternative disciplineswill be explored due to a dearth of correctional literature linked speciﬁcally to therapeutic correctional relationships, though a critical discussion will occur relating to the extent to which relationship knowledge can be applied to correctional settings.