Much previous research has considered experiences of bereavement and loss in a prison-based setting. This overshadows the nature of bereavement within the context of community supervision and probation delivery, resulting in inadequate explorations of the potential link to persistence and/or desistance from crime. Research into desistance has predominantly focused on relationships with those who are still alive. This article evidences an emergent theme of bereavement experiences within the context of probation delivery, relationships and desistance. It draws upon narrative research undertaken within a Community Rehabilitation Company in the north of England, collected as part of a doctoral thesis. Evidence demonstrates the similarities between the process of desistance and that of bereavement with the narratives of men and women reiterating how bereavement can influence the onset of criminal or risk-taking behaviour whilst highlighting emergent evidence on how bereavement can disrupt desistance. This enables the article to highlight the importance of resilience in the process of both bereavement and desistance.