What about languages other than English? I speak fluent French. I'd take the confidential document, use Babblefish to make a rough translation, correct any transaction errors, and then do what I want with the document. If French is too common, try Finnish or Albanian. This would certainly be an easy way to defeat the system, or at least in my opinion.
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GTB Inspector is the answer!
GTB Inspector is capable of multi-protocol outbound content monitoring with real time enforcement and without need for rights management software.
French smench
The majority of the Internet, and especially the offensive stuff, is in English. Anybody can effectively manage and secure their network with a combination of monitoring, policy training and enforcement without spending the thousands of dollars for a Websense yearly license.