Introduction. Managers from road freight transportation organizations were interviewed on barriers and facilitators to implementation of occupational health, safety, and well-being interventions for aging heavy vehicle drivers. As aging drivers are more likely to be seriously injured or die in a work-related incident than younger drivers, it is important to recognize strengths and weaknesses throughout the system to identify intervention that addresses their specific needs. Method: A Systems Theoretic Accident Model and Processes (STAMP) control structure was constructed to chart the controllers, controls, and feedback channels in the system to identify gaps in health, safety, and well-being intervention in the system. The STAMP control structure also charted the barriers and facilitators within levels across the system. Eleven managers were recruited into the study representing a range of road freight transportation organizations throughout Australia. Results: Interview data revealed that barriers and facilitators existed at most levels of the system. Facilitators included advice from external agencies, support from upper management, modern technology, and regular social communication with drivers. Barriers were a lack of guidance on aging issues, operational conflicts with health and safety objectives, and the drivers’ fear of disclosing health information associated with their driving role. In regards to formalized intervention in place to support aging heavy vehicle drivers, the system is reliant on fitness to drive medical assessments based on age and jurisdiction. Conclusions: As there was generally a lack of senior direction cited from the upper levels of the system on aging issues, there was much variation across the study on how aging risks are managed in the workplace for heavy vehicle drivers. Practical Applications: This study recommends that managers across the road freight transportation industry receive formalized aging-awareness health and safety training in how to manage work-related driving hazards for aging heavy vehicle drivers.