The topic in this paper is how former special needs students with academic competence from upper secondary school succeed in education on a higher level. The study concentrates on students who at their start in upper secondary education were registered with problems of concentration, difficulties in reading, writing or mathematics. The main part of this paper will base on qualitative interviews with nine former special needs students. Seven out of the nine informants were registered with reading and writing difficulties. However, it is also possible to compare these informants with longitudinal data from a larger group of students who have been followed prospectively since spring 1996. Theoretically the study is based on life course research with special emphasis on social transitions. In transitional processes between different educational arenas gatekeepers often play important roles. This study will examine how such gatekeepers, e.g. teachers, may facilitate or obstruct these transitions for a vulnerable group like former special needs students.