Previous research examining differences in levels of well-being between leaders and nonleaders has yielded mixed results. To explain the inconsistencies, we compare levels of well-being among nonleaders, mid-level leaders, and high-level leaders. Drawing from the job demands-resources model (Bakker & Demerouti, 2007, 2017) and the expanded version proposed by Crawford et al. (2010), we anticipate mid-level leaders will have lower levels of well-being compared to senior leaders and nonleaders, and females will be more vulnerable than males in mid-level leadership. In Study 1, we use multilevel models and propensity score matching (N = 24,067) and find mid-level leaders have worse general health conditions compared to nonleaders and high-level leaders, and that this effect is more pronounced among females. In Study 2, we collect experience sampling data from workers (N = 86; 1,634 observations) who completed a short survey four times daily for five consecutive working days. Mid-level leaders report more end-of-day negative emotions than high-level leaders and nonleaders, mediated by higher job demands and lower levels of job control to combat the negative effects of job demands; an effect that is particularly pronounced among female respondents. In Study 3, we use a two-wave time-lagged survey study (N = 330) and find middle managers have more challenge and hindrance job demands than nonleaders, and insufficient job control to offset the negative effects of job demands. Female middle managers report the most physical health symptoms and enjoy less eudaemonic well-being than their male counterparts. We conclude that leadership levels and gender have important and overlooked impacts on well-being. (PsycInfo Database Record (c) 2023 APA, all rights reserved).