We have an IPsec site to site VPN setup between PFsense at our local office, and TMG in our datacenter. This works for the default subnets at both office. Below are the subnets for the current IPsec.
Office: 192.169.0.0/22 (192.168.0.0 - 192.168.3.255 which covers all 3 private adapters on pfsense)
Datacenter: 10.1.1.0/26 (10.1.1.0 - 10.1.1.127 This is the default subnet for the Internal Adapter on TMG)
The issue is we have a second subnet at the datacenter (10.88.1.0/26) that we need to include in the site to site route. I have added the subnet to the internal adapter, along with the network route. This works on TMG and I can ping the servers on that subnet.
On the PFSense side, I created a second PhaseII connection with the same local subnet (192.1688.0.0/22) and the additional subnet (10.88.1.0/26). Pfsense was able to connect both PhaseII connections with no issue. When I attempt to send traffic across the tunnel, it tries to use the correct access rule for the VPN, but fails with the following 2 errors:
"A socket operation was attempted to an unreachable network: 0x80072743 WSAENETUNREACH"
