Hours of service regulations govern the working hours of commercial motor vehicle drivers, but these regulations may become more flexible as highly automated vehicles have the potential to afford periods of in-cab rest or even sleep while the vehicle is moving. A prerequisite is robust continuous monitoring of when the driver is resting (to account for reduced time on task) or sleeping (to account for the reduced physiological drive to sleep). The overall aims of this paper are to raise a discussion of whether it is possible to obtain successful rest during automated driving, and to present initial work on a hypothetical data driven algorithm aimed to estimate if it is possible to gain driving time after resting under fully automated driving. The presented algorithm consists of four central components, a heart rate-based relaxation detection algorithm, a camera-based sleep detection algorithm, a fatigue modelling component taking time awake, time of day and time on task into account, and a component that estimates gained driving time. Real-time assessment of driver fitness is complicated, especially when it comes to the recuperative value of in-cab sleep and rest, as it depends on sleep quality, time of day, homeostatic sleep pressure and on the activities that are carried out while resting. The monotony that characterizes for long-haul truck driving is clearly interrupted for a while, but the long-term consequences of extended driving times, including user acceptance of the key stakeholders, requires further research.