This article provides a view of contemporary Australia in terms of patterns of offending and incarceration, the characteristics of its correctional systems, vocational education and training (VET) within correctional settings, and post-release employment of prisoners and offenders serving community-based orders (CBOs). A two-year case study of employment assistance for 2,458 Australian prisoners and offenders serving CBOs was evaluated. The voluntary 12-month programme targeted participants at moderate to high risk of reoffending. Overall, employment outcomes were positive with more than one-third of registrations resulting in employment. Employment outcomes varied for gender and participant status (prisoner/offender). Recidivism outcomes were analysed for the whole programme and for a random sample of 600 prisoner participants. Results indicated a very low overall recidivism rate (7.46 per cent) for programme participants, and comparison of pre-programme and post-release recidivism showed reduced recidivism on three recidivism measures. The findings are contextualized in terms of current thinking and emerging practices in offender treatment, with a focus on reintegration as ecological system engagement and integrated systems of support as central to promoting positive lifestyle change.