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General • OpenVPN not routing site to site?

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Having some issues getting a site to site connection working with OpenVPN and hoping someone can point me in the right direction.

The overall configuration is as follows:

Site A: pfSense with OpenVPN Server
LAN subnet: 192.168.20.0/24
Gateway: 192.168.20.1

Site B: Mikrotik RB5009 with OpenVPN Client
LAN Subnet: 192.168.3.0/24
Gateway: 192.168.3.1

I had no major issues getting the OpenVPN connection setup, following various tutorials out there. But once I have the connection established I can't communicate across the subnets, despite having appropriate entries in the routing tables.

The OpenVPN connection is setup with the private subnet 172.16.21.0/24 with the resulting configuration
Code:
          Mikrotik                      pfSense192.168.3.1 <-> 172.16.21.2 <-> 172.16.21.1 <-> 192.168.20.1
What's interesting is that the routing appears to be partial. From a machine on the pfSense LAN I can ping:
- the local gateway 192.168.20.1 (normal)
- the local side of the OpenVPN connection 172.16.21.1 (good)
- the remote side of the OpenVPN connection 172.16.21.2 (good)
- the Mikrotik gateway IP 192.168.3.1 (almost there!)
- but I can't ping anything else on the Mikrotik LAN

In the other direction, things get cut off sooner. From a machine on the Mikrotik LAN I can ping:
- the local gateway 192.168.3.1 (normal)
- the local side of the OpenVPN connection 172.16.21.2 (good)
- but I can't ping the remote side of the OpenVPN connection or anything further along the chain.

The overall configuration of the Mikrotik box is a little complicated since it's setup for Dual-WAN with automatic failover based on the configuration I've posted here:

https://gist.github.com/eableson/685f54 ... 96189811fc

On the routing front, everything seems to be correctly setup:
Code:
/ip route printFlags: D - DYNAMIC; I - INACTIVE, A - ACTIVE; c - CONNECT, s - STATIC, v - VPN; H - HW-OFFLOADED; + - ECMPColumns: DST-ADDRESS, GATEWAY, DISTANCE #       DST-ADDRESS         GATEWAY          DISTANCE 0  As   0.0.0.0/0           1.0.0.1                 1 1  IsH  0.0.0.0/0           208.67.220.220          1;;; ISP2 2  As   1.0.0.1/32          10.93.124.225           1;;; ISP1 3  IsH  9.9.9.9/32          192.168.10.1            1   DAc   10.93.124.192/26    ether2                  0;;; ISP2 4  As   94.140.14.14/32     10.93.124.225           1;;; ISP2 5  As   149.112.112.112/32  10.93.124.225           1   DAc   172.16.21.0/24      ovpn-out1               0   DAc   192.168.3.0/24      local                   0   DAv + 192.168.20.0/24     172.16.21.1             1   DAv + 192.168.20.0/24     172.16.21.1             1;;; ISP1 6  IsH  208.67.220.220/32   192.168.10.1            1;;; ISP1 7  IsH  208.67.222.222/32   192.168.10.1            1 8  IsH  0.0.0.0/0           9.9.9.9                 2 9  IsH  0.0.0.0/0           208.67.222.222          110  As   0.0.0.0/0           149.112.112.112         211  IsH  0.0.0.0/0           94.140.14.14            1
despite the documentation saying that openVPN's push route isn't supported, I am seeing the VPN routes showing up automatically.

Side note: The basis of this configuration is for eventually to have multiple sites using Zerotier as the connection but this site is a hosted environment and I can't drop in a switch or replace pfSense.

Statistics: Posted by InfraErik — Wed Dec 20, 2023 12:50 pm



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