A school-based program in an inner-city alternative high school was developed to intervene in the intergenerational transmission of trauma and loss as well as to improve patterns of attachment using psychoanalytically informed group and individual treatment. Students selected for admission to this school have a history of unsuccessful academic careers, social and familial difficulties, or a combination of these. Three groups (men, women, and adolescent parents groups) were formed as correlates to the existing support structure of the school. The groups met for one hour during lunch, which we provided. Participation was voluntary, although students could receive partial credit for regular attendance. The following case material was taken from the first three semesters of our adolescent parent group, September 2002 to January 2004.