I have a PC running Windows 7 as the host for a Ubuntu Server 12.04 VirtualBox-Guest installation. On this guest OS I installed OpenVPN following the tutorial on help.ubuntu.com. I am now running Mac OS X Mountain Lion with TunnelBlick and am trying to connect to the OpenVPN server without success so far.
As for the VirtualBox installation everything should be defaulted but port forwarding 1194 (and port 22 for SSH). I am also forwarding this port within my router to the host OS.

While I have no trouble connecting through SSH I can not get access to OpenVPN.

Is it even possible to have OpenVPN running inside a Guest OS and use it as a vpn?

What would be a good way to troubleshoot this connection?

migrated from serverfault.com Aug 23 '13 at 16:24

This question came from our site for system and network administrators.


The direct answer to your question is probably that you've forwarded port 1194 of the TCP protocol rather than UDP.

But the better solution is this:

Change the adapter to use bridged network then the guest gets direct access to the LAN without the requirement to implement additional port forwards Host->Guest.

Then port forward UDP/1194 from the internet/wan through to the IP of the guest on your lan.

If you're still having problems, post your tunnelblick connection log.

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