Here is the update, I switched from shared key to SSL and TCP to UDP, now it seems to be working. Will monitor this line for couple of days to see if I've further problems.

I think that you should see only the VPN call in WAN interface, once created the tunnel all comunications are between LAN and VPN interface.

yes, routes are ok, but you may need to configure also a firewall rule in pfsense or in local firewall in your server.

I'm in the same boat as you. I haven't been able to set this up in pfSense 2.0. Hopefully someone will have an answer at some point.

So, I tried replacing the Linux+shorewall router with pfSense, to see if it was something strange with how I was configuring the Linux client.  Still no joy.  Then I tried using IPsec instead of OpenVPN, and it worked!  This may be the first time in history IPsec has actually made something easier. ;)

Thanks for the response joako.  I will research and do what you suggest with the public network option.  I'm a little confused when you say the same CIDR.  Do you mean the same network/mask?  I am using two /24 from the private space 172.16.0.0; one for each side.  Thanks again!

EB

I've got file sharing working. For those of you interested in this setup, what I did was start a WINS server on my DC computer in the 10.0.1.x network. Then on the outside firewall I added the WINS server IP, DNS server IP, domain name, and domain search list under services–>dhcp server-->LAN. After doing this I was able to resolve internal websites, and access network shares from a client computer on the 192.168.15.x network.

Now that the test setup is working, I'll try adding a few more client "sites" to the mix and see what happens if I expand the setup a bit.

This guide is based on 1.2.3
In 1.2.3 there wasn't an option to specify in NAT rules a source.
What the guide is refering to, are the "external" and "internal" port.

In relation to the screenshot you posted:
The "Dest. ports" and "NAT ports" should be 1195, but the "Src. ports" should be any.

The other side of the site-to-site knows nothing about the roadwarrior subnet.
–>you need a static route to make the roadwarriors known.

I don't think you can use TAP in 2.0…. http://doc.pfsense.org/index.php/OpenVPN_Bridging

First of all, find out the IP address(es) that the hostname in question resolves to.

Then on pfSense1 create a static route for those IP addresses that routes through the OpenVPN tunnel. You'll need to ensure that both pfSense hosts know how to route to the LAN on the other side.

It works after changing the MTU only for the wan interface facing the proxy to 1200, 1300 won't work. Weird thing…