Multi-WAN OpenVPN Guide
This is a great illustration of both the value of purchasing pfSense support, and the benefits this will have for the community. One of many is it forces us to write documentation. 
Several customer inquiries have resulted in documentation, some of which is already public (the rest will come with time).
A customer was having trouble trying to get OpenVPN working on multiple WAN interfaces. This lead me on an endeavor that resulted in the following documentation on how to make this work.
August 6th, 2007 at 4:09 am
This is great! I even might get the support service my self. Is it turn key? Can i just say give access to the hardware and you build config? I’f like to know more how the whole support process works.
August 6th, 2007 at 3:55 pm
We commonly access customer systems via VPN, or the WAN side by having you add our public IPs to your WAN rules, or guide you through things using GoToMeeting sessions.
Feel free to email me (cmb@bsdperimeter.com) and we can discuss further.
June 13th, 2009 at 7:27 pm
Found this howto, and thought our prayers were anwered. Tried to set this up today…with much frustration. We got both server instances setup in pfSense, however, they both used the same gateway, instead of each server using its own gateway. When connecting to the second vpn server, the packets try to comeback via the gateway of the first server, and so the connection fails.
June 15th, 2009 at 3:18 am
skemp: Should work. I made a note to review that documentation though, that was quite a while ago and things may be different than it describes in current versions.
August 14th, 2009 at 3:54 am
This definitely still works using the same procedure as before. That page isn’t very descriptive though, there are potential gotchas that it doesn’t fully convey that some people may not catch. I clarified that page a bit.