This study provides a comprehensive examination of how the work-school interface relates to work outcomes such as task performance and job satisfaction. Additionally, this study builds upon past research by examining a range of work- and school-related resources and demands that collectively influence the work-school interface. Data were obtained from 170 working undergraduate students at multiple time points over the course of a semester, as well as from participants' supervisors at the organizations in which the students work. The strongest antecedent of job satisfaction, interpersonal facilitation, and job performance was work-school facilitation. Demands in one role create pressures in the other. Contrary to expectations, job demands positively related to work-school facilitation, while school demands positively related to school-work facilitation. For practitioners, this study highlights the need to better understand the interplay between school and work roles for employees at a time when continuing education is emphasized. Employers benefit from the performance gains and positive attitudinal shifts that stem from experiences of facilitation between roles. From a theoretical perspective, this study reveals a unique pattern of results that adds to our understanding of the dynamics involved in the integrated work-school routines of working students. This is one of the first studies to investigate the relationships between four bi-directional forms of the work-school interface and subsequent multi-source assessments of organizational outcomes. As such, it offers an examination of how conflict and facilitation from both the work and school domains relate to work outcomes.