This paper reports conversational interviews with key stakeholders in order to analyse the critical role of the treating medical practitioner in the management of injured workers with a registered WorkCover claim in South Australia. The comments expose the dilemma of treating general practitioners in their dual roles of “gatekeeper” and service provider against a backdrop of the ongoing demands and pressures from claims agents, vested interest groups, litigation, pervading antagonistic process relationships, inflexible work settings and the preoccupation with containing costs. The study highlights the need for treating medical practitioners to understand the WorkCover system and legislation. It is suggested further that their practice would benefit from holistic management, supportive care, clear language, respectful communication, timely medical updates and helpful professional attitudes. It was noted that many medical practitioners favour some redesign of medical management practice encompassing the development of a leadership role and the provision of progressive medical management plans in order to maximise successful return-to-work outcomes for injured workers.