One of the most fundamental problems in computer security is protecting sensitive digital information from unauthorized disclosure. There are a number of challenges, such as spyware, removable media, and mobile devices, which make this a very hard problem. The problem becomes even more difficult when the adversary is somebody who is authorized to view the data. This is what is commonly referred to as an insider information leak. Insider leaks often occur out of malice, but sometimes are just due to plain negligence, as was the case with a recent leak of 26 million U.S. veterans' names, birth dates, and social security numbers. Current systems make an attempt to protect against this type of disclosure, but use rudimentary techniques that can be easily bypassed by a knowledgeable attacker. Examples include disabling "print" and "save" menu options within an application or scanning network traffic for signatures of known sensitive content. This paper examines a n...