Background: Across Europe and the Nordic countries, unemployment among 18–30 year-olds is a major challenge, which in some countries is being tackled by focusing on education. In Denmark, young unemployed people or people on the margins of the education system are assessed regarding what is known as an ‘education requirement’. Hence, education has become compulsory as a requirement for unemployed young people who claim social benefit. Purpose: This study argues that in order to understand the variety and complexity in young people’s movement between education, training and jobs, we have to understand how those are embedded in current sociocultural conditions. Drawing on social constructionist theory, we analyse the interaction between the young people and the wider context. Method: The article is based on qualitative analyses of focus group interviews with 62 young people in training programmes aiming at helping young adults into upper secondary education. Qualitative interviews were conducted across the country at 12 different projects. Four case projects were identified in order to conduct more in-depth fieldwork. Data were analysed qualitatively. Findings: Overall, the analyses depict how a somewhat disorganised educational market, a changing labour market, a rapidly increasing tendency to diagnose, as well as increased demands related to performance, position the young people on the margins of the educational system. The analyses suggest that the young people’s ways of interacting with structural conditions are formed by ‘disorientation’, ‘lack of work’, ‘diagnosing’ and ‘vulnerability’. Conclusions: According to the research presented, we suggest that it is necessary to address and develop more transparent pathways through education, and find new ways of solving the problem of a lack of apprenticeships. There is a need to devise solutions that involve the labour market more closely, address issues of the noteworthy increase in ‘diagnoses’ and how this affects young people, and find ways of reducing the pressure on young people in educational systems in general.