The investigative setting for this study was an alternative educational program that serves at-risk middle and secondary school students. The study evaluated students' conceptual understandings of forgiveness, their exercise of forgiveness in the face of perceived school-related transgressions, as well as the relationship between the two variables and student mental health and well-being. Overall, the students' cognitive grasp of forgiveness was found to be less sophisticated than was demonstrated by a similar sample of adults, indicating that the students, as a group of externalizing youth, struggled to use forgiveness to resolve relational conflicts. Specific factors that may foster forgiveness in habitually aggressive youth are presented along with recommendations for interventions.