Although leading others is undeniably stressful, scholarly work in leadership contexts thus far focuses more on the consequences of leaders? stress for their subordinates or employees in general. Surprisingly scant research on stress carryover in leaders yet exists. Drawing on conservation of resources theory, we nurture this perspective by studying how the work-related stress of leaders affects their off-the-job stress, thereby turning to the mediating role of insomnia. We further consider how segmentation supplies and telework alter the overnight stress carryover in leaders. Based on multilevel analysis of 637 observations from 115 leaders, we find evidence that the stress experienced by leaders during work leads to heightened off-the-job stress. Although we do not find work stress to result in increased off-the-job stress through insomnia, we identify this indirect effect to be jointly shaped by segmentation supplies and telework. Notably, we show that receiving stronger segmentation supplies help leaders mitigate their stress carryover via insomnia on days when they telework but not when they work from the office. Our findings contribute to a deeper understanding of work stress creeping into the private domain of leaders. We discuss implications for future research, acknowledge limitations, and offer recommendations for human resource professionals.