Recent interest in terrorist risk assessment and rehabilitation reveals that the likelihood and risk factors for terrorist disengagement, re-engagement, and recidivism are poorly understood. In this presentation, I review related literature on criminal desistance, disaffiliation from new religious movements, commitment, and turnover in traditional work organizations, role exit, and the investment model to develop a series of theoretical starting points for gauging the likelihood and predictors of risk, which can help inform evaluation efforts. I then highlight key findings from the existing literature on terrorist disengagement and re-engagement/recidivism as well as key differences across samples and the methodological challenges associated with such research—mainly the absence of control groups, relatively small sample sizes, the need for a lengthy time horizon, and inconsistencies in what constitutes re-engagement and recidivism. Then, using data collected on 185 terrorist engagement events for 85 individuals representing over 70 unique terrorist groups, I present my and my colleagues’ findings on the drivers of terrorist disengagement and re-engagement. We find that terrorist disengagement is a lengthy process more commonly driven by “push” rather than “pull” factors, specifically disillusionment with the strategy or actions of the terrorist group, disillusionment with leaders or other members, disillusionment with one’s day-to-day tasks, burnout, difficulty living a clandestine lifestyle, difficulty coping with attacks, and psychological distress. Importantly, “de-radicalization” is only cited as playing a “large role” in just 16% of disengagement events in our sample. I then discuss how one’s role within a terrorist group offers insight into the disengagement process. Our research shows that leaders and violent operatives have a harder time disengaging than those in logistical or support roles because of the sunk costs associated with their involvement and/or the fewer opportunities available to them. We also find that individuals in certain roles are more/less likely to experience certain push/pull factors for disengagement. I conclude by discussing our research on terrorist re-engagement, which shows that in the short term, a deep commitment to the ideology, maintaining ties to individuals still involved in terrorism, and being young increase the likelihood one will return to terrorism.