In this research, we examine the relationship between employee psychological entitlement and employee willingness to engage in unethical pro-organizational behavior. We hypothesize that a high level of PE—the belief that one should receive desirable treatment irrespective of whether it is deserved—will increase the prevalence of this particular type of unethical behavior. We argue that, driven by self-interest and the desire to look good in the eyes of others, highly entitled employees may be more willing to engage in UPB when their personal goals are aligned with those of their organizations. Support for this proposition was found in Study 1, which demonstrates that organizational identification accentuates the link between PE and the willingness to engage in UPB. Study 2 builds on these findings by examining a number of mediating variables that shed light on why PE leads to a greater willingness among employees to engage in UPB. Furthermore, we explored the differential effects of PE on UPB compared to counterproductive work behavior. We found support for our moderated mediation model, which shows that status striving and moral disengagement fully mediate the link between PE and UPB. PE was also linked to CWB and was fully mediated by perceptions of organizational justice and moral disengagement.