With the need for rapid school reform amid changes in socioeconomic and political situations, evidence abounds that today's school principals operate in a stress-strained environment. Participants of this study identified at least a form of stress on the job. More than 96% claimed to have experienced work-related stress at a level they believed was affecting their mental and physical health, work habits, and productivity. With continuous frustrations and challenges, many principals are thinking of quitting or seeking early retirement. The seven major stress factors identified were unpleasant relationships and people conflicts, time constraints and related issues, crises in the school, challenging policy demands and overwhelming mandates, budgetary constraints and related issues, fear of failure, and negative publicity and dealing with media. Coping tips were explicated from the perspectives of behavioral modification cues, physical exercises, relaxation techniques, professional help, and medical care. Through interviews with 52 principals in Connecticut for about 2.5 years, this article brings to the fore various causes of stress in school administration as well as some coping techniques for principals. Implications for school districts, enhanced leadership preparation practices, and further research are also discussed. (Contains 1 table.)