Mental health problems are among the main reasons why young people have problems with finding and keeping jobs. Poor mental health is also a major cause of dependence on disability benefits among young adults. In our research project we have indications of mental disorders (as measured by the HSCL-10) when our respondents – 216 former students with special educational needs – are 33 to 34 years. The main topic of this paper is how mental health in the mid-thirties is influenced by learning difficulties, behavioural problems, and psychosocial difficulties registered in adolescence, in this case at the age of 17 – 18. We also investigate the effects of relevant school variables, for example type of class and the use of teaching assistants. Moreover, the paper discusses theoretical and methodological challenging of retrospectively mapping the life course trajectories of vulnerable individuals, for example youth with experiences from orphanages and foster homes. In addition some data will be presented from a longitudinal study of former students with special educational needs who are in their mid-thirties and are clients of the Norwegian Labour and Welfare Administration.