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I've looked at a lot of VPNs, and "what's my ip address" sites confirm that outsiders can't tell where I really am when I'm using them, but I haven't been able to get my own WiFi yet, so I don't know what privileges they have. Can they tell that a proxy server is being used by their network, even if the person using it is obscured?

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Yes, and you may not be as obscured as you think. They can't tell what you're saying to a VPN server (because it's encrypted), including what sites you're accessing via the VPN, but they can tell that you are connecting to that VPN server. In networks where you have to register your device to your name somehow (e.g. many university networks), they can also tell that it's you (or someone impersonating you) who is connecting to the VPN.

For an example: I have laptop A, an account on VPN server B. I want to say "hello" to site C.

  • If I talk directly to site C, a network administrator can see "A said 'hello' to C".
  • If I talk directly to site C over an encrypted connection (e.g. over SSL), a network admin sees "A said 'oewqhfch' to C" (where 'oewqhfch' is 'hello', but encrypted; the network admin can't decrypt it)
  • If I use B as a simple unencrypted proxy to talk to C (i.e. I'm not encrypting what I say to B), the admin sees "A said 'Tell C "hello" and send me C's response' to B"
  • If I use B as an unencrypted proxy but encrypted my communication to C, the admin would see "A said 'Tell C "oqewqer" and send me the response' to B" (this is uncommon)
  • If I use B as a VPN (encrypted connection to B), the admin sees "A said 'ewqrvqfqjpocn' to B". B then decrypts that to see that A asked it to "Tell C 'hello' and send me the response", but the administrator of A's network doesn't know that A said that.

So, a VPN gives the benefit that everything you're doing on the VPN is hidden from the administrator of your network; the idea is to make it as though you were directly connected to the VPN provider's network. But your network administrator still sees that you're talking to the VPN server, because they have to route your packets to and from that server.

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  • So they definitely know I'm doing something, but they have absolutely no idea what it is? That doesn't seem too bad; I've been worried that they definitely knew what I was doing but might/might not know I was the one doing it. – RONeil1989 Nov 3 '14 at 20:06
  • Additionally, if the network administrator also handles C (or C admin asked him), he may see that "A user connected to B" around the same time that "a random person using B connected to C". The link between A and C could be much easier to establish than what would be needed for a theorical proof. – Ángel Nov 3 '14 at 21:36
  • FYI: I wouldn't worry too much about what the admin sees (unless you are doing something bad, or possibly dealing with highly sensitive data such as logging in to your bank). I would worry more about what potential hackers can see going over the network (e.g. someone trying to intercept your bank login credentials). Encryption is good because it hides such information if implemented correctly. – Jonathan Nov 4 '14 at 18:51
  • @Jonathan What the admin sees is a potential issue if you have a habit of connecting to open wifi networks, especially if you don't make absolutely sure there is supposed to be a wifi network there. Likewise, if you don't trust the admin (or if you're doing something bad, which you mentioned). But the wonderful thing about proper encryption is it protects against anyone besides the intended recipient intercepting the communication in transit. – cpast Nov 4 '14 at 22:24

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