Although the relationship between developmental dyslexia (DD) and the risk of occurrence of internalizing symptomatology has been widely investigated in the extant literature, different findings have been reported. In this study, two experiments with two general purposes are presented. The first study investigates whether the differences in the severity of internalizing symptoms between DD and controls are greater in students attending secondary school than in those attending primary school. Sixtyfive DD and 169 controls attending primary and secondary school took part in the first study. The diagnosis of dyslexia was obtained from standardized reading tests; internalizing symptom severity was assessed with the Self Administrated Psychiatric Scales for Children and Adolescents questionnaire. The results showed that adolescents with dyslexia had an increased level of self-perceived anxiety, depression and somatic symptoms, whereas no significant differences between DD and controls emerged in childhood. In the second study, a cohort of adolescents attending secondary school (DD = 44; controls = 51) was closely analyzed to clarify whether contextual and subjective factors could contribute toward exacerbating the risk of internalizing symptomatology at that age. Internalizing symptom severity was assessed with the Child Behavior Checklist, Youth Self Report questionnaire, decision-making factors were measured with the Melbourne Decision Making Questionnaire, and student's quality of life was gaged using the Clipper test. The results showed that high levels of internalizing symptoms in DD were associated with a low level of self-esteem and the tendency to react to problematic situations with hyperactivation. By contrast, positive relationships with peers were associated with low symptom severity. In conclusion, the intensified internalizing symptoms that could emerge in adolescents in association with the presence of dyslexia are predicted by social protective and risk factors that are associated with symptom severity. Accordingly, the results suggest that remediation programs for dyslexia should include implementing motivation strategies, self-esteem enhancement activities and building peers networks that, starting in childhood, can prevent the appearance of internalizing symptoms.