This article considers the challenges associated with completing risk assessments in countering violent extremism. In particular, it is concerned with risk assessment of those who come to the attention of government and nongovernment organizations as being potentially on a trajectory toward terrorism and where there is an obligation to consider the potential future risk that they may pose. Risk assessment in this context is fraught with difficulty, primarily due to the variable nature of terrorism, the low base-rate problem, and the dearth of strong evidence on relevant risk and resilience factors. Statistically, this will lead to poor predictive value. Ethically, it can lead to the labeling of an individual who is not on a trajectory toward violence as being “at risk” of engaging in terrorism and the imposing of unnecessary risk management actions. The article argues that actuarial approaches to risk assessment in this context cannot work. However, it further argues that approaches that help assessors to process and synthesize information in a structured way are of value and are in line with good practice in the broader field of violence risk assessment.