After all these years VPN technology is still frustrating. I spent hours yesterday and today trying to setup two different VPNs. One was IPSEC site to site and the other was openvpn.

The Site to Site was started yesterday. I was between to Sophos XG routers. I wasted quite a bit of time setting it up only to find out that both devices needed to be on the same firmware. This morning I updated the firmware on both routers and I was able to connect. Stability seemed fine on my side but the connection on the other end seemed a bit sluggish.

This leads me to OpenVPN. Have used OpenVPN for several years but only off and on. I have setup a number of OpenVPN servers but always on linux.

The goal for this setup was to setup a High Availability (HA) Cloud-based Asterisk system with a local Asterisk system. Apparently the key to get the master to fail over to the slave is they both need to be on the same subnet. I got them to sync but I couldn’t force the failover.

Working with this garbage called Windows Server 2008 I have failed miserably. I don’t have a linux server to use on this site. Well, I do but it’s already running the PBX in the VM and that is what has become highly unstable. Not sure why as I have the same setup working great in other locations. Hyper-V on this server is also very poor.

I also want to say that I am not even going to bother with PPTP. It’s never been reliable enough.