Dropping out of school before achieving any qualification is a serious problem both at an individual and societal level. This study provides an insight into the lives of young people who have dropped out or are at a risk of dropping out of vocational schools in Estonia and gives an overview of the reasons behind the interruption of their studies. The study is based on in-depth face-to-face personal interviews in 10 Estonian vocational educational institutions with those who have interrupted vocational training, those in danger of interruption and representatives of vocational educational institutions. Qualitative content analysis was used to analyse the interviews. Personal, family-related, school-related and economic reasons for leaving school as well as possible measures to prevent dropping out of vocational schools are discussed.