Heavy vehicle drivers are required to adhere to prescribed regulatory driving and rest hours within SA. Drivers have been the traditional recipients of enforcement attention where fatigue, speeding or other road safety concerns are apparent. ?Chain of Responsibility? legislation reforms are pending to better hold accountable others within the transport chain who are in positions where they can directly and negatively influence the on road driving task. SA Police have experienced practical difficulties in subjecting others within the transport chain in prosecutions relating to the recurrent incidence of driving hour breaches and inappropriate scheduling within the confines of existing legislation. This paper will provide an insight into the complexity that such investigations incur. The practical difficulties encountered by investigators and prosecutors will be discussed, and an indication of the necessary elements at law which are essential for enforcement efforts to be appropriately directed towards others beyond the driver.