So after a lot of trial and error I figured out what the problem is, especially because of the situation where connecting via the stunnel immediately after a reboot would fail, then by connecting directly to the OpenVPN server it would work, and finally by connecting via stunnel again after successfully connecting direct, it would work. I poured through the logs of both before and after and found a difference in the routing table. When connecting the second time, direct to the OVPN server, an additional entry was made to the routing table which was the IP of the VPN server /32 via the gateway of my WAN connection. The first connection didn’t have that route and subsequent connections did. So I went ahead and rebooted the AR750, connected to the VPN, added that route manually, and… didn’t work. Not to give up I left the route, disconnected and reconnected to the VPN and lo and behold, it worked… via the stunnel like I wanted. But that doesn’t mean I’m out of the woods yet. Something happened to the WAN link a few minutes later, such as maybe re-associating with another AP (on the enterprise wifi) or something because the connection was reset, the firewall and routes were re-loaded, and OpenVPN errored out and never re-tried to connect. At this point I had to re-add the manual route and then manually connect to OpenVPN again. That worked.

So that begs a few questions / things I have to look into…

  • I need the OpenVPN via stunnel profile to add the IP address of the VPN server as a route via the gateway of the WAN. For now I manually put the IP in there but on other networks that IP will be different. I’ll have to somehow reference the currently connected WAN gateway. And then I’ll have to add that either in the ovpn profile or call it from a script maybe? Not sure why that’s happening anyway.

  • Something is happening to DNS on the AR750 that it’s not functioning. The clients that reference the IP of the AR750 don’t get DNS responses and sure enough from ssh on the AR750 DNS doesn’t work. I changed the DNS server in /etc/resolv.conf to my gateway on the remote VPN server which is a DNS forwarder and then nslookup from the AR750 started working but the clients still weren’t getting responses from the AR750. So then I manually changed the DNS servers on both clients and everything started working perfect.

  • Stability of the wifi WAN link seems to be in question although, particularly in an enterprise wifi environment where there are multiple WAP’s. Possibly when roaming to a different AP the connection drops hard, kills my manually added route, and OpenVPN never tries to reconnect automatically. I’m wondering what I can setup to mitigate this scenario.

Any help would be very much appreciated. I know now what I’m trying to do is possible and I’m just about there.