My university wifi has no restrictions for web sites, however I can not SSH or using remote desktop. I solved this problem by using VPN.
Now at my dormitory I'm behind a proxy with same problem. My question is, is there any way to bypass this proxy by sending all traffics through VPN? I'm using Mac and the VPN service is PrivateInternetAccess which also support SOCKS5
Edit:
This is my first time I'm using proxy and I realised that I can use SSH. I just didn't configure it correctly.
This is not necessarily a simple question to answer because it depends on a lot of variables.
If the proxy is relatively simple, the easiest way round - if you have access to the server outside the network - is to change the port for SSH, a good thing to do anyway since having port 22 exposed on the internet will get you constantly probed by botnets. Port 443 is generally always available through proxies and the proxies generally expect not to be able to decipher the traffic and so will often let SSH traffic through. You can do something similar for remote desktop.
If you can get SSH to work, many other things can be made to work simply by creating suitable tunnels.
On the other hand, more sophisticated network security devices don't just provide a simple proxy, some even go as far as both deep packet inspecting and dynamic risk scoring. Such devices might well detect SSH traffic even on non-standard ports, they might also try to do a man-in-the-middle attack by substituting their own certificates instead of the correct end point cert. This might prevent a simple work around.
If you set up a local SOCKS proxy, you will still need an encrypted tunnel. Either a full VPN solution or a simple SSH based tunnel approach as outlined.
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