OpenVPN Routing Not working

tompark · Apr 16, 2020, 1:40 PM

Hi Guys,

I am having a bit of a strange issue with my OpenVPN Configuration and routing. When trying to traceroute from my remote network (subnet b) to my local network (subnet a) I am unable to get a route to client computers.

Network Configuration is as follows;

Subnet A (local network)

Router: 172.16.0.1
PFSense (hosting OpenVPN): 172.16.0.3
Local Subnet: 172.16.0.0/24

Subnet B (remote network)

Router: 10.0.0.1
PFsense (hosting OpenVPN): 10.0.0.1
Remote Subnet: 10.0.0.0/27

OpenVPN Subnet:
172.21.0.0/29
Subnet B: 172.21.0.1
Subnet A: 172.21.0.2

When I trace route from subnet A to Subnet B it works fine from client to server (10.0.0.6) and client to router (10.0.0.1).

When I try and do a traceroute from Subnet B to Subnet A at patricianly works as per the results below:

Traceroute from 10.0.0.6 to 172.16.0.50 will go as far as 172.21.0.2 and then times out.

Traceroute from 10.0.0.6 to 172.16.0.1 works fine
Traceroute from 10.0.0.6 to 172.16.0.3 works fine
Traceroute from 10.0.0.1 to 172.16.0.1 works fine
Traceroute from 10.0.0.1 o 172.16.0.3 works fine
Traceroute from 10.0.0.1 to 172.16.0.50 works fine

I don't understand why the Traceroute from 10.0.0.6 to 172.16.0.50 doesn't work, I have tried configuring and upstream gateway on the same 172.16.0.3 interface on the PFSense Box but this doesn't resolve the issue.

I am guessing there is a missing route somewhere but I can't figure out where that is and how to resolve the issue.

Does anyone have any suggestions that might help fix this issue?

Regards,