This study examines school dropouts from the perspective of male adults themselves through interviews with offenders currently serving sentences. Participants were 10 Portuguese male inmates, between the ages of 19 and 46 years of age, incarcerated in two prison facilities on the Azores. Qualitative and interpretative methods were carried out using a semi-structured in-depth individual interview that was audio-recorded and conducted on the basis of a list of topics. Interview transcripts and thematic analysis were used in data treatment and analysis. The findings primarily indicate that poor academic achievement and emotional and behavioural difficulties of participants played a particular role in early school dropout. The trajectories that these individuals followed within the education system presented problem behaviour, learning disabilities and/or foster care interventions. While school dropout circumstances were apparently various, analysis showed that they were underpinned by three distinct sets of conditions generally not addressed by the education system. The analysis of the triggering factors and the maintenance dynamics of school dropouts indicated three distinct types: retention/absenteeism, life turning points and positive resolution. Implications for secondary prevention and screening practices are discussed. (Contains 7 notes, 2 tables, and 1 figure.)