Boarding schools are the common 'out-of-home' placements for adolescents, due to various historical, religiously orthodox, and traditional reasons and due to dysfunction within families. The purpose of the current study is to examine the relationship between a free versus an enforced decision to enroll in a boarding school in terms of personal well-being among emancipated graduates. Ninety alumni graduates (aged range 20-41) of out-of-home boarding schools in Israel were recruited during 2019. Participants were administered a self-report anonymous questionnaire consisting of the following measures: Free versus enforced decision to enroll in a boarding school, retrospective satisfaction with the boarding school, personal well-being and traumatic events. Results indicated that a free decision to enroll in an out-of-home boarding school was associated with current satisfaction with social relationships but not with quality of life. Additionally, the longer the period spent in a boarding school, the higher was the satisfaction from the period at school. Older graduates reported less satisfaction from school retrospectively. It was concluded that involving the adolescent in life changing decisions such as leaving home to a boarding school is likely to influence the person's well-being during and after emancipation.