The current study examined the applicability of Frone’s model of work–family relations to work–study relations. The contribution of internal and external antecedents to conflict and facilitation relations between work and study was tested. The model also includes the effects of these relations on academic and psychological health outcomes. The participants were 661 Israeli working students (M age = 26.08, SD = 3.18). Structural equation modeling (SEM) analysis indicated an adequate index fit, suggesting that aspects of conflict and facilitation relations coexist when blending work and study. Number of working hours and financial support predicted conflict relations that, in turn, lowered grades, negatively affected further academic plans, and increased depression. Work salience, social, and academic support predicted facilitation relations, encouraged further academic study, and boosted grades. Results emphasize the advantage in examining conflict and facilitation relations simultaneously when investigating career development and psychological health of working students.