Ssh proxy to my private server. Squid proxy behind Tor. You might know I'm doing something, but what exactly I'm doing. No way. (Taking reasonable precautions to prevent DNS leakage, etc)
At that point though, it doesn't matter. If company policy says you can't use anonymizing proxies or can't SSH out or can't mask your traffic in any way, you're hosed right there. And most enterprises would have an employee handbook that says that. Immediately you're in breech of guidelines and misusing company resources.
So many people in this thread are trying to argue ways to hide your traffic. All I'm saying is, no matter how clever you get to hide what you're doing, you're in breech of your terms of employment from the very first step. No matter how clever you get, I've seen people fired based on my report that they were using SSH to get to their private server. Doesn't matter if they were checking their email or if they were hiring a hitman on Silk Road.
Enterprises don't care what you're doing, they care what you're not doing, and what you're not doing is the job they paid you to do under the terms you agreed to do it.
So many people in this thread are trying to argue ways to hide your traffic. All I'm saying is, no matter how clever you get to hide what you're doing, you're in breech of your terms of employment from the very first step. No matter how clever you get, I've seen people fired based on my report that they were using SSH to get to their private server. Doesn't matter if they were checking their email or if they were hiring a hitman on Silk Road.
Enterprises don't care what you're doing, they care what you're not doing, and what you're not doing is the job they paid you to do under the terms you agreed to do it.