Orthopaedic injuries of the upper extremity remain common, often requiring prolonged immobilization after surgical or nonsurgical management. Upper extremity immobilization often has a profound effect on a patient's daily life, including one's ability to safely operate a motor vehicle. Current literature on the safety of driving while immobilized is varied, although above-elbow immobilization of the upper extremity is generally thought to present a particular hazard to safe driving. Unfortunately, as common as this situation is, currently little to no guidance exists for patients, physicians, or lawmakers with regard to deciding whether a patient is safe to return to driving with upper extremity immobilization. Similar discord exists with the issue of patient and physician liability in such cases. In this review, we seek to present both historical precedent and a contemporary update of this complex, though a frequently encountered situation.