09:16
@Billy Deep packet inspection would still recognize it was a VPN, regardless if the contents is encrypted or not. Sure, we wouldn't be able to find what exactly they were doing, but it would still be blocked.
Any web traffic through the proxy also had to be signed with our own cert, which comes back to the initial problem of wanting to install certs
but hey, not my problem. I'm not paid enough to worry about those things :P