moored99 wrote
The service doesn't fail or show as an error in the event logs where do I start trying to debug this or is this a know issue with OpenVPN and Server 2008 x64.
I have no idea if it is a known issue, but to start debugging I would try specifying a log file for openvpn with --log <path to file>
maybe that will tell us why the service doesnt want to start on boot but works after when you start it manually