This study examined the relationship between psychosocial work characteristics and educational disparities in health. Informed by the evidence on the relationship between work pressure and higher education, we suggested reframing the distribution of psychosocial work characteristics in the context of education. We differentiated psychosocial work resources from demands and hypothesized that the inconsistent mediation effects of psychosocial resources and demands are associated with educational status. Using data from the 2008 National Study of Changing Workforce (NSCW), we found that psychosocial work resources and demands had inconsistent mediating effects on the education–health relationship. Higher educated employees were more likely to report autonomy, challenge and schedule control, but they were also more likely to experience overtime hours, job overload and work–family conflict. Work resources appeared to protect higher-educated workers from stress and health problems while work demands put them at risk of less favorable health outcomes. In addition we found that the ‘costs’ of psychosocial work demands were stronger among women, particularly those who were highly educated, suggesting that highly educated women did not reap the full health benefit of high educational attainment. Our findings illustrate that the observed positive associations between education and health mask important heterogeneity in the effects of psychosocial work characteristics. We discuss the implications of this study for health and family-based work policies.