School success may be minimal for students who have difficulties building social relationships and ultimately fail at developing social competence. As a result, social skills training is often provided to increase prosocial interaction. Despite evidence of the effectiveness of teaching appropriate social functioning, there is concern about generalization and maintenance of learned skills. In this article, we first describe the problems with current social skills instruction for students who exhibit challenging behaviors and lack of generalization data. We then introduce and provide examples of strategies to program systematically for generalization and maintenance to achieve social competence for students with emotional disabilities and/or challenging behavior.