Learning disability in adolescence is a complex phenomenon caused by multiple factors. Given this presupposition, this paper aims at investigating the characteristics of the family and school contexts in which adolescents with learning disabilities are inserted. A qualitative study guided by the Multiple Case Studies method (Yin, 2005). Three adolescents and one of their parents participated in this study. The adolescents' ages ranged from twelve to thirteen years old, two of them were females and one male. As research instruments, the investigator used the Academic Performance Test (Stein, 1994), Resources Inventory Home Environment (Marturano, 2006) and Semi-structures Interviews. The results revealed that a comprehensive understanding of this phenomenon is necessary, even if the teenagers and their mothers emphasize in their identification of the disability only issues regarding characteristics of the adolescents and their relations with their teachers in the classroom.