Perceptions of employee entitlement are reported to be increasing in organizations and have been linked to negative outcomes at work. Employee entitlement is an employee’s belief in deserving preferential treatment or reward without regard to performance. Arguments, however, are emerging that entitlement may also be linked to positive behaviors. In this article, we outline a study that examines the moderating effect of self-monitoring on the relationship between employee entitlement and organizational citizenship behavior and affective organizational commitment. Based on survey data collected from 167 individuals, we found that self-monitoring moderated the relationship between the specific subscales of employee entitlement and organizational citizenship behavior but had no relationship to commitment. Although previous studies have addressed entitlement perceptions as a negative outcome for the organization, in this article we outline the potential for positive outcomes. Limitations and future research directions are outlined.