This study utilized latent profile analysis (LPA) to examine patterns of principal stress and coping and its relations with principal (n = 125), teacher (n = 3671), and student (n = 19,390) outcomes. LPA analysis of school principals based on their reports of stress and coping showed that most principals were classified as having high stress and high coping (74%) whereas 19% of principals were classified as high stress and low coping. Only a small percentage of principals (7%) were characterized by low stress and high coping. We also examined whether stress and coping profiles of school principals predicted concurrent and prospective measures of principal and teacher wellbeing and efficacy, principal and teacher perceptions of school climate, and measures of student behavior and dispositions. The principal latent profiles significantly predicted concurrent and prospective measures of principal and teacher well-being, with large effect sizes for prospective principal health (Cohen's d = 1.93) and satisfaction (d = 0.94), and a medium effect size for prospective teacher health (d = 0.68). Changes in principal health (d = 1.30) and satisfaction (d= 0.49) over time were also significant. However, the latent profiles did not predict prospective measures of principal and teacher efficacy, perceptions of school climate, and student classroom behaviors. The results of this study show that examining patterns of principal stress and coping together is important to understand and improve principal and teacher well-being.