jacksch
I opened a ticket on this in March, but I'll post the issue here as well to help anyone else who is experiencing this issue.
If you have adjacent subnets behind two different OpenVPN clients, for example 10.50.0.0/16 behind Client A and 10.51.0.0/16 behind Client B, and you enter those subnets into the corresponding user records in OpenVPN AS, it will not work. All clients will be pushed an aggregated route for 10.50.0.0/15. Routing tables on Client A and Client B will both have an entry sending traffic for 10.50.0.0/15 back to OpenVPN AS, creating a routing loop.
If you use only one of them, it will work.
If you use 10.50.0.0/16 and 10.52.0.0/16, the routes will not be aggregated and will work correctly.
So far the only workaround is to manually override the routes at both Client A and Client B to send traffic out the local interface and hope that the overlapping routes work. 🙁
