This mixed-methods study examines the working conditions and well-being of Kentucky principals through surveys (N = 66), focus groups (24 principals and 15 superintendents), and analysis of the Impact KY Working Conditions Survey (2023–2024). The well-being crisis among school principals is not merely an individual concern but a systemic issue operating at school, district, and state levels, with far-reaching implications for schools and students. Findings reveal a profession under significant strain, with principals reporting inadequate support to meet the complex demands of an ever-evolving role. Key themes include excessive workload, professional isolation, emotional exhaustion, and the 24/7 nature of the principalship that threatens sustainability in the role. Principals cite time constraints, compliance burdens, and lack of work-life balance as primary barriers to effectiveness and well-being. The Impact KY data revealed significant perception gaps, with principals rating working conditions 19–33 points higher than teachers, suggesting leadership may not fully recognize the depth of challenges facing both principals and staff. Both principals and teachers identified resources and emotional well-being as areas of greatest concern. The study documents how compliance requirements, inadequate staffing, and limited mental health supports contribute to principal burnout and attrition. Findings call for strengthened mentorship systems, policy streamlining, increased operational support, and coordinated well-being initiatives across state agencies, districts, and universities to ensure principal effectiveness and retention.