proxy detection and bridge?

My office has a monitor proxy and security, where they can watch what you do on your PC … I recently had upload an attachment to a friend from the server in the office, a Word file via Hotmail and Hotmail is one of the sites blocked in my office, now my question is very simple and many of them know the answer, but not me ….. i know they can control where I have visited, etc. .. But what I know is that they can know that any file I uploaded via email, and do not ask what kind of proxy or security they use, etc, coz i dont know … just a simple question that can be known attachment and what I sent, that particular file … thanx

They can control all traffic and attachement if not encrypted. To avoid to attempt to do this using a VPN service as a proxy Slicky SSL to encrypt all their traffic.

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