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The present study is aimed at analyzing the quality of the relationships with educators, as well as the attachment mental representations among adolescents living within residential communities and coming from disrupted families.Based on attachment theories and their therapeutic applications, this longitudinal assessment tried to cross-check the hypothesis that being cared by secure educators could improve the insecurity and the disorganization of adolescents’ Internal Working Models of attachment.Our results, as the sample is a restricted one, only partially confirmed our hypothesis. Even if the adolescents’ state of mind toward attachment appeared improved, their daily interactions with the educators were still disengaged and devaluating. Moreover, the educators could not really be considered as attachment figures, due to the fact that the institutional organization doesn’t allow them to vouch for the continuity and stability of their presence.