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:
    2. Router:
    3. DNS Server:
  2. Host Only network for the tunnel
    1. IP:
    2. Router: Empty
    3. DNS Server:

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@
hutber@Jamies-Mac ~ $ //ssh access to guest

When connected to VPN

hutber@hutber ~ $ ssh -L 3333:github.someprivateurl.net:22 hutber@
.... (hangs)

1 Answer 1


add the -v option to the ssh command to get a verbose output of what is happening and provide that back to be able to better see what the issue is.

Since i got Jeff a little upset, It may be related to MTU - check this link out and see if you expiernce the same issue.



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