At the global level, school dropout represents an important concern of specialized research within the educational issue as a whole, a fact explained by the very high percentage of young people who do not complete their studies. Every school organization tries to own and successfully implement an effective school dropout management system to achieve the expected results, in accordance with the harmonization of the needs, interests, aspirations and expectations of the entire school community, but also of the society in general. This study aims to identify differences in the challenges faced by stakeholders dissatisfied with the dropout management (N=96) and those in the highly satisfied group (N=260). A series of statements were evaluated by the participants and the comparison was accomplished with the help of t-test for independent groups. We confirmed statistically significant differences for all challenges presented.