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When subordinates violate a policy, authority figures have to decide whether to be strict and make them face the consequences or be lenient and not enforce the policy. In this chapter, we argue that when an authority figure treats a subordinate leniently, that subordinate is more likely to develop an elevated sense of entitlement, which then has various negative consequences for the authority figure and the subordinate’s group members. Drawing on the literature on the sources and consequences of psychological entitlement, we put forward propositions relating to authority leniency and subordinate entitlement. In summary, we propose (a) that single acts of leniency may lead subordinates to feel entitled to future leniency, (b) that repeated leniency may lead subordinates to develop a general sense of entitlement, and (c) that leniency and the resulting entitlement can have many negative consequences such as increasing group conflict and causing low performance. We report preliminary results in support of some propositions. For example, we show that leniency that can be attributed to something external to the subordinate may prevent the subordinate from feeling entitled. Last, we call for additional research. We hope that our chapter will cause authority figures to consider the consequences of treating subordinates leniently, including the possibility that the subordinates will subsequently feel entitled.