Prior research has framed bootlegging as employees’ unofficial innovation that occurs without organizational authorization or official support. In this paper, we call for bringing leadership back into the study of antecedents of bootlegging and examine the effects of leadership context, specifically leader humility, on employee bootlegging. Following the conservation of resources (COR) theory, we propose that leader humility can provide valuable endogenous resources, such as relational energy, for employee bootlegging. We also propose that work unit structure (organic versus mechanistic) can serve as a boundary condition in this relationship. We test our hypotheses in (i) a scenario-based experiment, (ii) a three-wave time-lagged study with a sample of 212 employees, and (iii) a three-wave time-lagged study with a sample of 190 employees embedded in 20 teams. The results show that leader humility positively relates to relational energy, which, in turn, causes employee bootlegging. Furthermore, an organic structure strengthens the relationship between relational energy and bootlegging, and the indirect effect of leader humility on employee bootlegging via relational energy. The paper concludes with a discussion of what these findings suggest for future research and managerial practice.