So you settle down in your hotel room to connect to your home or office network. You get on the Internet from the hotel room and initiate a connection back to your base station . . . and nothing happens. After ten or fifteen seconds you cancel the connection attempt and try again. Still nothing. You verify that your laptop is on the Net (the GRC.com web site comes up just fine. :) So you try again to connect to your home base . . . but OpenVPN can't connect.

What's wrong?

Something about the configuration of the local hotel's network is blocking your connection attempts. They might have the default OpenVPN port 1194 blocked by their network firewall (if that's the port you are using). But it appears that whatever port you are using is having no success.

What's the solution?

The entire goal for a remote connectivity solution is a robust and reliable means for connecting no matter where you find yourself. So the more different possible ways you have to connect the greater the chances that you'll be able to find at least one way to reach your home base no matter what network conditions separate you.

The standard way

Actually, the standard way is to neither recognize nor solve this problem at all. I have never found any resource that talks about running multiple simultaneous instances of the OpenVPN server in order to be able to accept incoming connections on multiple ports and protocols.

So most people fire up only one copy of OpenVPN, choose to have it use either the TCP or UDP protocol, and probably leave its default port set to 1194. They assume, if they ever stop to think about it, that they'll never have any trouble connecting to their machine from wherever they may be in the world.

Perhaps if they are always lucky they'll be right. Or perhaps they run across a remote network that, for whatever local administrative reason, blocks their sole means of access. Then they're out of luck. As we saw above, to have the greatest chance of establishing a connection back to home base it's useful to create more than means of connecting:

The complex way

Untortunately, the current release of OpenVPN (v2.0.5) only allows the user to specify a single protocol (TCP or UDP) and port number for the server to listen for incoming connections. Allowing multiple simultaneous listening ports is trivial from a programming standpoint, but the problem doesn't seem to be on the OpenVPN developer's radar. I would do it myself since OpenVPN is open source. But that would fork the source and cause lots of other problems.