The provision of an adequate liability regime for ADAS technologies is an essential prerequisite for its roll out over the coming decade. Facing to the challenge of future highly automated vehicles, this paper proposed a Human-Machine Transition (HMT) approach as a common conceptual framework for considering Human Machine Interaction (HMI), liability and ethical issues in a unified way. The issues that arise are interrogated from a legal perspective, more specifically liability regimes and that of applied ethics. The paper highlights the issue of the handover/takeover. Potential consequences for insurance companies are then identified accordingly, with the aim to progress towards the sustainable deployment of automated vehicles on public roads.