The present study analyzed concurrent and predictive validity of single-item scales for assessing principal stress and coping. We examined concurrent and prospective relations among stress and coping single-items with principal job satisfaction, overall health, perceptions of school safety, and principal leadership self-efficacy. We also compared principals and teachers on their stress and coping levels using the same single-item scales. Consistent with the literature on teacher stress and coping, the correlations of principal coping with different outcomes-job satisfaction, overall health, leadership efficacy, and safety perceptions--were stronger in comparison to the correlations between principal stress and those same outcomes. In regression models with both stress and coping, only principal coping predicted concurrent and future principal job satisfaction and overall health, as well as change in those outcomes. Coping also predicted concurrent but not future perceptions of school safety. Stress and coping did not consistently predict concurrent or future measures of leadership self-efficacy. Last, we found that principals reported even higher levels of stress than the well-documented high levels reported by teachers. We discuss areas for further research and potential use of these measures.