Australia's mineral, resource and infrastructure sectors continues to expand as operations in rural and remote locations increasingly rely on fly-in, fly-out or drive-in, drive-out workforces in order to become economically competitive. The issues associated with employing these workforces are becoming more apparent and include a range of physical, mental, psychosocial, safety, and community challenges. Research evaluating the impacts of fly-in, fly-out operations in Australia has been limited, and in February 2013 the Australian House of Representatives Standing Committee on Regional Australia made 21 recommendations aimed at improving these operations. To date, none of the recommendations have been implemented. The Construction and Mining sectors, in which most FIFO workers are employed, represent 12% of the total Australian workforce. Recent evidence from Safe Work Australia (2013) notes that serious injuries incident rates in both these sectors are well above the national injury rate. In addition the median payment and compensation cost for serious injury in these sectors are considerably higher than the Australian average due to higher employees salary, severity of incidents, lengths of absence from work, and medical expenses. These at risk remote site FIFO employees are further challenged post injury by lack of access to well-regarded disability management processes that have traditionally closely involved the workplace in the rehabilitation process. This paper examines the disparate challenges faced by both employers and employees in workplace wellbeing in remote sites, and raises questions as to how best disability management professionals can design, implement, and evaluate effective rehabilitation processes for injured FIFO workers who are a fast growing segment of the workforce but who work in conditions hitherto atypical of mainstream industry.