First of all, being able to circumvent policy is not the same as allowed to do that, and different yet from a good idea: I'm pretty sure, with such policies, circumventing them would be punishable.
- e-mail: Certainly intercepted
- browsing: Almost certainly intercepted
- SSH and other workarounds: might work, but if USB devices and smartphones aren't allowed, I'd guess outbound communication will be limited (i.e. "it probably won't work"). Also, might not be allowed.
Even if you manage to get a tunnel up, passive traffic analysis will flag you: "This Tony guy has no outgoing connections, except these: long-lived, all to the same host, high-traffic, encrypted." Good luck persuading your employer ('s lawyers) you were not squirreling away the company's databases (having willingly and knowingly circumvented company policy isn't going to win you any points either).
6I hope you did not post this from work, or now they'll watch you even closer. – None – 2010-06-21T08:12:42.387
1Remember too that this monitor has to justify his existence. A nice, juicy policy violator is his raison d'être. So not only is your monitor well placed, he's strongly motivated. – msw – 2010-06-21T08:42:03.110
Yes man, I said my new company, I am not in there now, lol. – Sawyer – 2010-06-21T08:56:43.783
1I presume that attempting to circumvent your monitoring policy is itself a violation of the policy? They'll eventually catch you. "Hey, so why does this guy have 2 gigs of ssh data in and out every hour?" – msanford – 2010-06-27T22:44:57.450
Tunnel traffic through ssh if you reallllly need a way. – Chris – 2010-08-26T20:44:46.350