There is great value in not only exploring how relationships are formed and the mechanisms that lie beneath them, but also how they can be severed and disrupted over time. It is suggested within psychotherapy that a positive relational outcome is not simply relative to the characteristics of the practitioner, but more closely associated with the successful resolution of relational ruptures (Safran and Muran, 2003). For example, Horvath and Marx (1991) described the course of the relationship, as a sequence of developments, breaches and repairs that are normal and prevalent within any therapeutic relationship. This chapter will examine relational ruptures within the context of corrections, drawing on the outcomes of primary work, to establish what ruptures are and how they can be successfully repaired within practice. Luborsky (1984) proposed that the strength of a therapeutic relationship is its capacity to work through internal and external stresses without breaking down, with both players persisting due to their shared dedication to the goals that have been set. In this way, Luborsky (1984) highlighted that relationships function as a way to overcome obstacles in one’s self, a notion that has also featured within Maruna’s (2001) work in relation to desistance. This chapter proposes that relationships work in a way that facilitates growth and can be used to stimulate growth with respect to identity transformation. It also highlights the additional challenges of ruptures when they are situated within a correctional context, proposing ways to address such challenges. This chapter is organised into two parts: the ﬁrst part introduces and addresses ruptures within probation practice, and the second part considers ways in which ruptures can be managed, in light of this knowledge.