This study examines the interaction between subordinates’ workplace status and supervisors’ humility in shaping psychological entitlement and its downstream effect on expedient behavior. Drawing on self-regard motive theory, we propose that supervisor humility moderates the status-entitlement relationship by activating distinct self-regulation strategies. High-status subordinates under high-humility supervisors develop entitlement through self-enhancement, while low-status subordinates under low-humility supervisors exhibit entitlement via self-protection. Three-wave survey data from 48 supervisors and 235 subordinates supported our hypotheses. Multilevel analyses revealed that supervisor humility significantly moderates the status-entitlement relationship: high-humility supervisors amplify entitlement among high-status subordinates, while low-humility supervisors escalate entitlement among low-status subordinates. Additionally, psychological entitlement was positively associated with expedient behavior, with a significant moderated mediation effect. These findings challenge the assumption that high workplace status alone drives entitlement, highlighting the critical role of contextual factors like supervisor humility. Moreover, the study uncovers an unintended consequence of humble leadership, revealing that humility can exacerbate entitlement and expedient behavior of certain employees. This research also offers practical insights for managing entitlement and ethical conduct in hierarchical organizations.