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This study explores discrepancies between parent and student perceptions of school well-being in Italian vocational schools and their relation to behavioral risk. Using matched data from 95 student–parent pairs, it employs the School Well-being Questionnaire (QBS) and Strengths and Difficulties Questionnaire (SDQ) to compare perceptions and assess emotional and behavioral issues. Results show that parents consistently report higher well-being than students, particularly regarding relationships with teachers. These discrepancies are wider among students with individualized education plans (PDPs) and correlate with elevated behavioral difficulties. The findings suggest that perceptual mismatches can signal early signs of risk. This study highlights the value of multi-informant perspectives in educational contexts and contributes to a preventive, relational understanding of student vulnerability.