For women administrators in higher education, workplace factors like managing multiple roles; work bleeding into personal life; issues with leadership; discrimination and marginalization; and role insufficiency (i.e., ambiguity in work roles and reduced sense of control) contribute to increased workplace stress. Individual coping responses are often determined by how stressors are perceived indicating whether an individual will effectively or ineffectively manage a stressor. The purpose of this study was to examine the relationship between stress and health risk among women in administrative roles in higher education with a particular focus on coping strategies employed. The results suggest that women administrators are employing effective strategies when dealing with daily work stressors and have developed a degree of learned resourcefulness; however, health data indicate long-term potential for mental health issues. Further results suggest a dichotomous view of the role of leadership as both a cause of stress and a strategy for effectively managing stress.