Empowering leadership has been widely recognized as an effective approach for stimulating employee vitality in previous research. The prevailing positive theoretical views of empowering leadership fail to provide sufficient explanations for the phenomenon that managers in practice often find or worry that they are unable to experience positive support from the empowered employees. Therefore, this paper draws upon the self-enhancement theory to explore the mechanisms underlying the potential diminishing effect of being empowered on employees’ upward supportiveness. The results from two scenario-based experiments (i.e., Study 1A and 1B) and one multi-source field study (i.e., Study 2) reveal that perceived leader empowering behavior and perceived leader favoritism orientation interact to induce employees’ psychological entitlement, which in turn reduces their upward process feedback-seeking behavior, and consequently diminishes their upward supportiveness. Such effects are statistically significant when employees perceive a higher level of leader favoritism orientation and do not exist when employees perceive a lower level of leader favoritism orientation. This paper adopts a new theoretical perspective to reveal the potential adverse consequences of leader empowering behavior. In doing so, it answers scholars’ call for a more dialectical understanding of empowering leadership and also responds to managers’ demand for more knowledge that can help them comprehend and mitigate the risks associated with their empowering practices.