The rail driver workplace is full of challenges for effective health management, posing a significant threat to the sustainability of the industry. In Australia, train drivers undergo periodic health assessment as part of a nationally standardised approach to reducing sudden incapacitation risk; however, studies suggest that the current assessment protocol is not operating as effectively as they might. To improve this, there is a need to understand the experiences of drivers undergoing workplace health assessments, and how they engage with them. Drawing on research of known barriers and enablers of positive health status, this study sought to examine train drivers’ perceptions and experiences of recurring organisational health assessments and how they subjectively engage with this process. Five focus groups with train drivers (n = 29) were held across four Australian rail organisations, seeking to gain their understanding of the National Standard and their attitudes towards health assessments. Transcript data were subjected to thematic analysis. Preliminary findings identified four primary factors: drivers’ unmet information needs, low perceived assessment reliability and validity, need for psychological assessment and support, and the use of maladaptive assessment-threat avoidance strategies. This paper presents an overview of these preliminary findings and suggests that driver engagement with health assessment may be improved by proactively addressing these factors in occupational health initiatives and preventative interventions to tackle the growing problem of train driver health impairment.