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I am trying to SSH tunnel in a guest VM that will connect to a VPN and give access to the host to otherwise blocked urls. All access is correct regarding keys.

  • Host = Connecting via the ssh tunnel (Linux)
  • Guest = Connects to VPN and is being tunneled to. (OSx 10.13)

Guest has 2 network cards.

  1. VPN network
    1. IP: 192.168.238.130
    2. Router: 192.168.238.130
    3. DNS Server: 192.168.238.2
  2. Host Only network for the tunnel
    1. IP: 192.168.138.130
    2. Router: Empty
    3. DNS Server: 192.168.138.1

No connection to VPN

When I am not connected to the VPN I can connect to the guest very easily:

hutber@hutber ~ $ ssh -L 3333:github.someprivateurl.net:22 hutber@192.168.138.130
Password:
hutber@Jamies-Mac ~ $ //ssh access to guest

When connected to VPN

hutber@hutber ~ $ ssh -L 3333:github.someprivateurl.net:22 hutber@192.168.138.130
.... (hangs)
  • Can you connect (no tunnel) to your host via SSH? – Allan Jun 20 '18 at 14:37
  • I cannot. I can't connect at all when the guest is connected to the VPN. – Jamie Hutber Jun 20 '18 at 15:17
  • Your VPN provider (work perhaps?) is blocking SSH. – Allan Jun 20 '18 at 15:19
  • Interesting... I actually have this same image at home and it works perfect. However at work I connect through a "guest" wifi network, which I then connect to the VPN. The guest network connects to ssh without a problem. – Jamie Hutber Jun 20 '18 at 15:37
  • A question then, I am not trying to access external ip's, just my host to access the guests network. I guess the VPN could block port 22? Even though at home with the same setup they don't block port 22 from working. – Jamie Hutber Jun 20 '18 at 15:38

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