The purpose of this study was to measure teacher well-being and assess specific ways administrators affect the physical and mental health of staff. A modified PERMAH Workplace Survey was administered in response to a significant decline in annual climate survey results postpandemic. Key findings were analyzed through the lens of the Areas of Worklife Model. The data from 104 PreK-12 teachers in a suburban New England district indicate several specific ways teachers can be best served by leaders who are intentional in designing and cultivating organizational systems that prioritize the mental, physical, and social health of teachers. The prevalence of conflicting responses speaks to the complex nature of teacher self-efficacy and the ways stressors can undermine positive feelings about the job while also highlighting the value of tools like the modified PERMAH Profiler to assist school leaders.