It's not a routing issue, it's a bug/mis-feature in FreeBSD's IPSec stack.
See https://doc.pfsense.org/index.php/Why_can%27t_I_query_SNMP,_use_syslog,_NTP,_or_other_services_initiated_by_the_firewall_itself_over_IPsec_VPN for more info.
-Adam




On 04/24/2015 09:37 AM, Gregory K Shenaut wrote:
I have two pfSense boxes connected via an IPSEC tunnel.

I'm confused about whether a route gets added automatically to the remote 
network end of an IPSEC tunnel when the tunnel comes up. I was under the 
impression that there was no need to be concerned with routing between the two 
subnets within the pfSense boxes, that they would “know” about a remote subnet 
and route to it automatically.

However, currently the tunnel can be up, hosts in either remote subnet can ping 
each other, but the pfSense boxes themselves can't ping hosts in the remote 
subnet, including the LAN address of the other pfSense host to which they are 
connected.

And if I do add a static route, what should I use as the gateway? Devices in 
the local subnet just use the LAN address as the gateway, but that doesn't seem 
appropriate for the pfSense box. The tunnel goes out over the WAN address, but 
using that as the pfsense box's gateway to the remote subnet doesn't seem right 
either.

While in this anomalous state, if I look at the IPSEC status, I see the correct 
networks in Local subnets and Remote subnets in both boxes. Both boxes have 
only a “pass all ipv4” firewall rule for IPSEC. If I look at the routing 
tables, there is no route to the remote subnet.

I also have dead peer detection enabled, which if I understand it correctly, 
requires that the other side's LAN address be pingable.

What could cause this situation, and what is the solution?

Thanks for any suggestions.

Greg Shenaut
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