In recent years, there has been a proliferation of programs aimed at preventing radicalization and disengaging known violent extremists. Some programs have targeted individuals through the use of case management approaches and the development of individual intervention plans (e.g., the Desistance and Disengagement Program and the Channel program in the UK; the Australian New South Wales Corrections Proactive Integrated Support Model—PRISM—and state-based division initiatives in Australia). There is a broad consensus in the literature that the evaluation of such initiatives has been neglected. However, the evaluation of case-managed interventions to counter violent extremism (CVE) is challenging. They can have small caseloads which makes it difficult to have any comparison or control group. Client participation can vary over time, with no single intervention plan being alike. This can make it hard to untangle the relative influence of different components of the intervention on indicators of radicalization and disengagement. In this presentation, results from primary research that set out to evaluate case-managed CVE interventions in Australia and develop evaluation metrics are presented. This research involves the examination of interventions implemented by New South Wales corrections and state police. The effectiveness of these interventions was assessed against a five-point metric of client change. Client change overtime was analyzed using case note information collected by the various interventions on client participation. Results show that client change is not a linear process and that the longer an individual is engaged in a case-managed intervention, the more likely they are to demonstrate change relating to disengagement. Specific case studies are used to illustrate trajectories and turning points related to radicalization and to highlight the role of case-managed interventions in facilitating disengagement. Key elements of effective interventions include the provision of ongoing informal support. Investment in capturing case note information should be a priority of intervention providers. Different challenges confronted by case-managed CVE interventions are highlighted.