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Setting up an OpenVPN server is not as easy as you might think, at least for the first time and specially if you want to have the traffic routed throught the VPN. Now this isn’t another HowTo, just a quick word on the situation that I currently have at my house, if anyone has any suggestions or questions just post them and I’ll take a look at them.

So I set to the task of creating a VPN
server using OpenVPN on my home server. At first it seamed rather easy
task to accomplish, but as I would later find out it wasn’t like that.
Since I have two Sun Netras at home I decided to have one of them as a
dedicated server and to install all of the necessary services on this
machine and to leave the firewall just to protect the network from
intruders.

So the first thing I try is to get the systems connected without any
encryption or anything special, then get them connected using
encryption with static keys and both methods work as they should, I can
even SSH to the other machine. So now I just have to configure the
server to get the system working. After reading the HowTo on the
OpenVPN site, which it truly lacks information as far as to what the
commands or options do exactly, I was able to set up the server with a
simple configuration using encryption, but it didn’t work. As it turns
out the keys were created the wrong way and they weren’t signed. So I
had to clear everything and recreate the keys, this lead to the VPN
working and being able to SSH into the server through the VPN.

Now I continue with getting a second machine connected to the server
and being able to SSH between the clients, this was successful and it
was working as expected. So when I try to get to the Internet it fails,
so what I try to do is simply reconfigure the VPN to have it route the
traffic to the firewall and apparently I’m unable to get that working.
After doing a research on Google it turns out that there isn’t much I
can do, because if I enable the routing directive it turns out that the
traffic will get routed to the VPN server and there apparently is no
way to route it to another point. So currently I have it configured as
a tun interface and the traffic is getting to the server and then it’s
being routed, not encrypted, to the firewall. This is currently working
but it’s not how I would like for it to be set up.

Now when I tried to hook up the other two machines in my network it
turns out that OpenVPN has trouble working under Windows XP Home, which
is a major drawback since the only way to get them working would be to
upgrade those machines over to Windows XP Pro. After trying a couple of
times I was able to get one of the machines to connect to the VPN and
be able to get out to the internet. Now I’m still working on getting
the other machine connected to the VPN. What did I do on that one
machine to get it connected to the VPN, I don’t know, but I do know
that I did power down the system completely and then powered it up and
also set it up with a static IP, which doesn’t really work, then change
it back to a dynamic IP.

One would say that the easiest way would be to upgrade those
machines to Windows XP Pro, but the issue is that there is one machine
that will connect to the VPN which is running Windows XP Home and it’s
located miles away from me and the person that’s using it is not
technical to be able to go through a Windows Installation. So I have to
get the damn thing working. So my question right now is “Why does the
Home edition of Windows exist?” I mean it’s just a pain in the neck to
get it working on a network. So I’ll make a mental note to only
purchase Professional editions of Windows.

So far I have both laptops (one is Windows XP Home and the other one
has Ubuntu 6.10) and my desktop machine (Windows XP Pro) hooked up to
the VPN without any problems. I’m still working on getting the second
desktop machine hooked up to the VPN as well as my laptop on Windows
MCE (my laptop runs Windows MCE and Ubuntu 6.10).