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A friend of mine wants to use a VPN on his school's Wi-Fi becuase they've blocked many applications such as Skype, etc.

My question is, if he uses a VPN (with iOS 7) will the system administrators be able to see he's using a VPN and eventually disable it?

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Yes, VPN traffic is easily distinguishable on the network, and yes, it can also be easily blocked if the admins care for some reason. So, "a friend of yours" shouldn't really do it to circumvent IT policies. :)

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  • Thanks. What's with the quotes "" tho..? – William Edwards Sep 22 '14 at 16:48
  • Oh, just the usual "asking for a friend" sort of reaction. Google for it. – mricon Sep 22 '14 at 16:51
  • OK... I'm really asking for a friend tho :P – William Edwards Sep 22 '14 at 16:53
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    "OK... I'm really asking for a friend tho :P" That's what THEY always say too. ;P – k1DBLITZ Sep 22 '14 at 17:58
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Look into setting up Stunnel, or a similar tool to wrap your traffic (VPN via TCP) in an SSL connection. The admin would have no way of knowing that this was VPN traffic, although it may be dropped by a web proxy or look suspicious if too much bandwidth was going through this connection. I've done it personally and it's worked great!

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  • That's not really an option for iOS 7, as the question implies. – mricon Sep 22 '14 at 19:19
  • Stunnel itself maybe not, but ssl wrappers yes, as my answer implies. – CurtBraz Sep 23 '14 at 15:52

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