Administering an institutional repository (IR) can be challenging. Aside from common but nuanced tasks such as explaining the difference between a publisher's PDF and a post-print or establishing ingest workflows for different kinds of content, IR administrators sometimes encounter situations that push at IR policy, call into question fundamental assumptions about the benefits of Open Access, or complicate the relationship among searchability, access, and an item's authenticity. When these situations arise, it is tempting to seek guidance from trusted sources; however, privacy concerns and other details specific to these requests can make it difficult or even impossible to discuss them with other IR administrators and colleagues or to find adequate help in the literature. These situations can leave one feeling professionally isolated and uncertain. In an effort to help provide some relief and bring awareness to the ubiquity of challenging IR requests and the kinds of careful consideration that they require, I will share some of the hard cases that I have encountered as an IR administrator, how I have handled them, and lessons learned.