Much research exists on the role of correctional staff on the carceral experience, but less work examines how staff influence post-release behavior among those previously incarcerated and how personal characteristics might be related to correctional staff attitudes and actions. This includes, for example, individuals’ perceptions of success upon release. The current study uses a sample of 427 detained juvenile males derived from the Australian Institute of Criminology’s Drug Use Careers of Offenders (DUCO) study to assess the relationship between individuals’ perceptions about the willingness of correctional staff to help them and their perceived likelihood of success upon release. Results indicate that most Australian juvenile detainees felt optimistic about their prospects for success upon release and that staff were interested in trying to help them. However, no relationship was found between the two variables of interest. Instead, time served was most significantly related to one’s perceptions of success upon release. These findings are discussed through the juxtaposition between Australian and American criminal justice systems and offer several implications for carceral policy.