Performance monitoring is a common tool used to align the goals of employees with those of owners. However, responses to monitoring mechanisms are likely to vary based on individual characteristics. This study examines how the increasingly prevalent personality trait of psychological entitlement interacts with performance monitoring to affect production and misreporting. Psychological entitlement, a stable and pervasive sense that one deserves and is entitled to more than others regardless of one’s actions, affects individuals’ interpersonal styles and motivations. Using a paper-based maze task, we find that for individuals who do not expect their performance to be monitored, production (misreporting) is lower (greater) as psychological entitlement increases. This result supports extant literature showing a correlation between psychological entitlement and negative organizational outcomes. In contrast, for individuals who have an expectation of performance monitoring, production (misreporting) is greater (lower) as psychological entitlement increases. Supplemental analysis provides evidence that psychologically entitled individuals’ heightened sensitivity to the opinions of others leads to an increase in impression management strategies when performance monitoring is expected. Our results suggest that performance monitoring is not only effective at limiting negative organizational outcomes of psychological entitlement, but can even bring out positive organizational outcomes for the entitled.