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This paper explores the challenges that correctional authorities encounter when dealing with the transition of offenders back into the community after the completionofterrorism-relatedsentencesorafterdemonstrating extremist views or associations. It draws on research conducted in the Australian state of New South Wales that examined mechanisms to sup port radicalised offenders exiting custody and completing a community based order (i.e., parole). Drawing on interviews (N = 55) conducted with correctional and other agency staffandterrorist inmates and parolees, the paper explores six issues: whether the radicalised cohort is unique in relation to supervision needs; engaging families; information sharing; assessing risk; the implications of the broader environment surrounding terrorism; and professional training and knowledge needs. Qualitative data indicate that radicalised offenders can have similar reintegration needs to mainstream offenders and that family assistance, while impor tant, has some drawbacks. The application of intelligence in the super vision context is highlighted, as well as its limitations. Data illustrate the emerging practices and practical limitations of risk assessment. Results show how the broader social and political environment can influence supervision processes, with topics related to staff training canvassed. Broader lessons for policy and practice on the community supervision and reintegration of radicalised offenders are highlighted.