A mixed methods approach was used to identify problem situations in peer and school contexts experienced by urban middle school students with high incidence disabilities that may impact their emotional and behavioral adjustment. A survey and semi-structured interview were conducted with a predominantly African American sample (95%) of 74 adolescents (61% boys) with high incidence disabilities (71% with learning disabilities, 15% with intellectual disabilities, and 14% with emotional or behavioral disorders). Focus groups were conducted with 35 school staff members. Based on the survey data, 14 peer and school problem situations were rated as frequently occurring and difficult to cope with. Data from the student interviews and focus groups revealed five themes of problem situations, including three in peer (i.e., peer influence, provocation, and teasing) and two in school (i.e., academic challenges and student–teacher relationships) contexts. These findings have important implications for school-based interventions focused on reducing risk for emotional and behavioral adjustment problems.