In the fight against Early School Leaving, many regular and alternative secondary schools design and implement particular measures aimed at supporting students at-risk and improving school engagement. Based on the analysis of 4 different measures implemented in mainstream schools and other 4 implemented in alternative learning arenas, this paper will question the impact of such measures on young adults’ trajectories in the light of the educational trajectories of 12 youngsters. These trajectories were constructed based on two longitudinal bio-interviews conducted with each youngster, with a time frame of approximately two years. The analysis of these 8 measures was anchored in interviews with their designers (principals), its implementers (teachers) and the target groups (students), and also in focus-group discussion with teachers and youngsters. The findings indicate that early school leaving and other at-risk trajectories are marked by many challenges and struggles. Even though these complex and difficult educational trajectories would benefit from the implementation of measures capable of providing support and increasing school engagement, the data indicate that such measures seem to fall short in achieving their objectives. Based on the confrontation between the needs expressed in youngsters’ trajectories and the analysis of these 8 measures, this papers offers practical insights for educational institutions on how to improve school engagement and avoid Early School Leaving.

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