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If I set up my own VPN or similar server on my always on computer at home, they say I could access gmail from my work computer. My question is, will the IT guys at work be able to notice something strange is going on if I'm on gchat at work through one of these things? (by IT guys I mean the two guys in charge of our network at work - its a small company)

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If they're looking, they'll see a lot of encrypted traffic going to that machine. They won't necessarily be able to read it, but they can probably just flip a switch and kill the connection permanently.

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"a lot"? gchatting will look like "a lot" of encrypted traffic? – confusedWorker Feb 24 '11 at 3:31
I suppose it will depend on how heavily you IM. – Ignacio Vazquez-Abrams Feb 24 '11 at 3:46
+1 May not need to be much. Just need to be unusual. Repeated outbound encrypted traffic may be unusual. As noted, they could just block you – Dave M Feb 24 '11 at 3:58

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