I need to SSH into a server which is only accessible when I am connected to a VPN (PPTP). Using my Ubuntu 13.03 virtual machine, this works perfectly. First I connect to the VPN, then I ssh into the server. I have recently created a new Ubuntu 14.04 VM and am trying to use this instead. I have no problems connecting to the VPN, and my internet browser shows that I have an IP address on the remote site, but I can't connect to the server - ssh simply times out. Does anyone know how I diagnose and fix the problem ? Many thanks in advance.

  • Did you check if your Ubuntu 14.04VM has any firewall rules blocking the traffic? Try disabling the firewall first and see if the ssh connection still times out. Also please update your answer with the output from ssh -v when you connect to your server. – devnull Oct 31 '14 at 13:08

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