Insecure jobs can be stressful, resulting in poor employee health, and employees’ perceptions of insecurity can be influenced by the way their leader treats them. Considerable research has assessed negative leadership styles as predictors of adverse employee outcomes. We instead focus on positive leadership styles to help provide a more complete view of the effect of job insecurity for employees. Specifically, we examine (1) empowering leadership and subordinates’ psychological resources as antecedents of job insecurity, and (2) subordinates’ sleep quality as a consequence of job insecurity. Four-waves of data with one-month intervals were collected from full-time employees in South Korea (n = 399) and the U.S. (n = 359). Structural equation modeling and comparison with alternative models assessed the mediating effects. Empowering leadership predicted subordinates feeling less insecure about their jobs via psychological capital, which in turn, predicted subordinates’ sleep problems. Overall, results showed the importance of resources (from empowering leadership and psychological capital) for employees’ sleep quality.