Teaching music can be very stressful. The music education literature includes investigations of sources of stress and suggestions for stress relief, although it lacks a consistent underlying conceptual framework for stress. Role stress—a framework for understanding stress related to workplace dynamics—has the potential to provide structure while accounting for the nuance and complexity of organizations. The purpose of this study was to adapt and develop psychometrically sound questionnaires and then collect data to test a model to determine relationships among role stressors, role stress, and other variables of interest. Participants ( N = 1,576) responded to items related to six hypothesized role stressors, specialization and teaching loads, holding multiple jobs, years taught, job satisfaction, organizational commitment, and intent to leave the current job. I analyzed the data using descriptive statistics, factor analysis, and structural equation modeling. Key findings included (a) strong relationships among role stress and negative occupational outcomes, (b) confirmation of four known role stressors but nonseparation of role conflict and role ambiguity in statistical models, and (c) weak relationships between role stress and model covariates (years teaching, within-specialization teaching, and having multiple jobs). These results have implications for current and prospective secondary music teachers, music teacher educators, and school administrators.