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"Definitely shame on your IT guys for not blocking outbound connections to your own proxy at the firewall"

So, are you going to try to distinguish between me using my https banking service and my VPS with sshd bound to ports 22 and 443?

In the EU you may find yourself in an legally ambiguous situation deploying the level of packet inspection required to achieve that.

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No. I'm going to have monitoring software installed on every piece of computer equipment in the office and run daily reports on installed software. The second I come across something not on "the list" I'm going to pull the network cable for you cube out of the switch and then confiscate your equipment. Have fun explaining any missed deadlines to whoever you report to.

Yep, that pretty much sums it up. But in a well-run network, they wouldn't be able to install the software in the first place.

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