Abstract: Conditionally and highly automated vehicles will require drivers to take control as a result of a non-emergency, such as a geographical, terrain, capability or design boundary. It is anticipated that these events will provide the driver with a sufficient amount of time to prepare themselves for the transition of control. This study explores conditionally and highly automated vehicle transitions of control by asking how drivers of differing skill levels (learner, intermediate and advanced) approach the task of designing an interface responsible for making transitions safer, more usable and more efficient. Three focus groups generated detailed designs for vehicle-to-driver transitions in an 1-h and a 10-min “out-of-the-loop” scenarios and transitions from driver to vehicle. Results show great variation in the approaches taken by each skill group (e.g., the reliance on visual interfaces for awareness assist and viewpoints on issues such as multimodal displays). Customization was a common theme throughout, with drivers desiring the option to adjust alert timings and modalities in which information is displayed. This paper presents these designs along with a detailed comparison of group designs and implements distributed situation awareness theory to discuss findings and draw conclusions.