WatchIT: Who Watches Your IT Guy?

System administrators have unlimited access to system resources. As the Snowden case shows, these permissions can be exploited to steal valuable personal, classified, or commercial data. In this work we propose a strategy that increases the organizational information security by constraining IT personnel's view of the system and monitoring their actions. To this end, we introduce the abstraction of perforated containers - while regular Linux containers are too restrictive to be used by system administrators, by "punching holes" in them, we strike a balance between information security and required administrative needs. Our system predicts which system resources should be accessible for handling each IT issue, creates a perforated container with the corresponding isolation, and deploys it in the corresponding machines as needed for fixing the problem. Under this approach, the system administrator retains his superuser privileges, while he can only operate within the container limits. We further provide means for the administrator to bypass the isolation, and perform operations beyond her boundaries. However, such operations are monitored and logged for later analysis and anomaly detection. We provide a proof-of-concept implementation of our strategy, along with a case study on the IT database of IBM Research in Israel.