Traumatic grief arises as a result of interpersonal trauma experienced as a betrayal of attachment. The distinct set of symptoms associated with it were first recognized in the 1990s. Losses associated with traumatic grief can be either death or non-death related. A variety of studies have demonstrated that many prisoners have suffered from losses and trauma throughout their lives, and in many instances they have never received any support or interventions to address resultant problems. This paper examines whether there could be a relationship between many of the maladaptive behaviours demonstrated by the prisoners (including substance use), mental illness and traumatic grief. Of particular importance is the exploration of whether the high rates of recidivism seen in many developed countries (and which in Australia have been reported as high as 77%) may be related to traumatic grief. This paper explores new concepts that may be relevant to the development of strategies to reduce recidivism.