A field study of 109 information systems (IS) managers explores the relationship among organizational characteristics, job satisfaction, and work stress. The results indicate that work overload is the major source of perceived IS work stress, followed by role conflict, job-induced anxiety, and then role ambiguity. Four organizational contextual factors—IS climate, clarity and sharing of organizational mission, quality of work life, and flexibility of organizational processes—were found to influence significantly work stress and job satisfaction as perceived by IS managers. As expected, job satisfaction was significantly related to Is work stress while IS technological sophistication was not related to IS stress or job satisfaction factors. Contrary to predictions, neither the clarity and awareness of organizational policies nor the quality of IS resources were found to have impact on any IS stressor.