The purpose of the study was to develop a grounded theory of the underlying social processes and/or other ecological factors that impact the effectiveness of skill acquisition for students with emotional and/or behavioral disorders in a Midwestern city in the United States. Theory development was based on in-depth investigation of five students with emotional and/or behavioral disorders (EBD), who were taught assertive communication skills. This study examined ecological factors impacting the learning of a new social skill and the socialization skills of students with EBD. Based on the findings of this study, three broad conclusions are offered: (a) students identified as having EBD had difficulty in learning and utilizing a new social skill; (b) a completely inclusive school setting for students with EBD was ineffective to meet student needs; and (c) surface behaviors were addressed instead of the causes of emotional and/or behavioral disorders. Recommendations were made for those involved in the educational process of students with EBD and for those interested in conducting further research.