Although rather neglected in published work on risk assessment, studies concerned with the role of stress in violent offending have pointed to the impact on coping and meanings of occurrences and circumstances in offenders' lives prior to offences against the person. It is possible to augment this picture with insights and methods from other areas such as the study of depression. From consideration of a range of literature, initial research and clinical experience the present chapter identifies a number of relevant processes (including reciprocal relationships between personal and contextual factors) and directions for future research. The chapter concludes by drawing parallels between the psychological challenges faced by individuals upon release from custodial environments and those who face other sorts of transition, such as former members of the armed forces.