Surveys have been the primary vehicle for identifying variables associated with special education teacher attrition. Survey research, however, does not reveal the contextual variables influencing decisions to stay in or leave the classroom. We explored variables related to teacher attrition by qualitative interviews with 14 current and 10 former special education teachers. Analysis of the interview data revealed differences in teacher characteristics and workplace conditions. Stayers were more committed to teaching students with disabilities, had a higher sense of efficacy, felt more prepared by their preservice and initial teaching experiences, and exhibited more effective coping strategies. Stayers and leaven were frustrated differentially by various aspects of the workplace, such as decision-making power, administrative support, and professional growth opportunities. We discuss these findings in light of future research.