This article examines the occupational outcomes reported from three traumatic brain injury (TBI) rehabilitation models: comprehensive neuropsychological rehabilitation, comprehensive neuropsychological rehabilitation and occupational trials, and supported work. It is argued that programming for occupational entry or reentry must include precise specification of barriers to rehabilitation outcome goals and systematic planning for skill generalization and maintenance. The Barriers Profile and the New Medico Barriers to Anticipated Rehabilitation Outcomes Scale are offered as tools to assist interdisciplinary treatment teams in identifying the number and magnitude of personal and environmental barriers to occupational resettlement. The use of these tools is illustrated with a case example. Finally, specific procedures for enhancing generalization and maintenance of treatment goals are discussed.