Risk assessment and prediction play a key role in decision-making in probation practice. Yet the practical application of risk assessment judgements can be impacted by a range of factors, with implications for people under supervision as well as for potential victims and the community. Furthermore, there has been a shift within probation training to remote and online learning platforms to support workplace development. This article describes an exploratory study assessing the capacity of technology-enhanced training tools for enhancing and improving risk assessment in probation home visits. The findings indicate that, despite the limitations of the research, virtual reality and 360° videos may be valuable tools for addressing a number of the inherent challenges facing current probation training.