This chapter presents the Estonian case to analyse the social ecology of the development of students in the case of the risk of dropping out from IVET (Initial Vocational Education and Training). The persistence of the interrelated problems, such as early school-leaving and drop out from vocational education, leaving education without qualifications, being vulnerable in the labour market and the risk of social exclusion, refer to the existence of a “wicked” or complex set of interrelated problems that are approached from the perspective of social ecology. Two key aspects of social ecology are discussed: the main institutional developments of the Estonian VET system with a specific emphasis on the institutional and macro-contextual factors that could affect vulnerable youth groups in VET, and the micro-level empirical research to better understand the proximal processes of learning and development of students that risk drop-out. The sample of students interviewed consisted of 20 students (14 female and 6 male) aged between 16 and 22 years, from different vocational schools and regions in Estonia and studying different specialities. The empirical analysis identified three clusters of students, representing three separate ecologies of vulnerable students. The ecologies reflect the different experiences in getting help, or not, in the surrounding environment, in the case of emerging problems, and the consequences of their self-agency capacities and their perspectives for their future life.