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How to use SSL tunnelling on OS X to give full internet access to some applications while you are on a restrictive corporate network?

Details:

  • you want to be able to access some restricted destinations and/or ports with some applications from your computer but you are on a restricted network (corporate) - Even using a Torrent client.
  • you have an AWS machine running Ubuntu that you can use as a proxy (and you can SSH to this machine)
  • You cannot create a full VPN because this means that you will loose access to your intranet and you do not want that.
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    Please be aware that doing this is a security risk, and if you are seen bypassing corporate firewalls (especially with torrent sites), you can get into serious trouble.
    – Matt
    Jul 20, 2012 at 14:50
  • Do you have a handle on the network routing needed to choose between intranet and internet or the basics of using SSL tunneling? If you have solved one of these - it will help someone propose a workable configuration of the other. (there are three questions here - basic SSL tunneling, basic network routing, and understanding both well enough to synthesize a solution to make both work for the situation...)
    – bmike ♦
    Jul 20, 2012 at 15:16

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You can create a local SOCKS proxy by using the dynamic port forwarding function of SSH by running ssh with the -D flag. This will tunnel all traffic of applications that use the local SOCKS proxy through SSH connection.

For example running ssh -D1234 user@host will open a SOCKS proxy on localhost port 1234 that you can direct your applications to.

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Assuming that you are running Lion or greater, I would recommend that you create an OS X virtual machine (using VMware Fusion or Parallels Desktop) and route that through a full VPN.

Alternatively, if you have a Mac at home, you could just use VNC or some other remote desktop solution and run your applications from there.

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