Objective: To describe the timing and factors associated with the occurrence of sentinel events (financial strain, difficulty accessing therapy, return to work, accommodation change and independent transport use) during transition to the community for individuals with traumatic brain injury. Design: Longitudinal cohort design with data collected pre discharge and at 1, 3 and 6-month follow-ups. Subjects: Individuals with moderate to severe traumatic brain injury (n = 127), discharged home from acute care and inpatient rehabilitation. Methods: Data were collected using self-report questionnaires (sentinel events questionnaire, Mayo Portland Adaptability Inventory-4, Sydney Psychosocial Reintegration Scale, Depression Anxiety Stress Scale). Logistic regression was used to identify factors associated with sentinel events. Results: The most commonly reported events were independent transport use and return to work, reported on 104 and 90 occasions, respectively. A longer hospital stay and poorer community integration were related to negative events (e.g. reduced therapy). The inverse relationship was seen for positive events. Links existed between sentinel events (e.g. previous financial strain increased the likelihood of this event in transition). Conclusion: This paper highlights the interplay between personal and environmental factors and life events in shaping transition experiences. Individualised service planning and monitoring of sentinel events is important to promote successful community transition.