I have a problem with an IPsec VPN setup in pfSense 2.0.2 that I wonder if 
anyone can help me solve.

I am trying to set up a pfSense IPsec VPN for mobile clients.  The clients will 
be using the built-in "Cisco IPSec" client in Mac OS X 10.7 and 10.8 to 
connect.  I have assigned the Virtual Address Pool as 192.168.5.0/24, which is 
disjoint from those on the pfSense gateway.  In my Phase 2 Tunnel definition in 
pfSense, I am using "Mode: Tunnel" and "Local Network: LAN subnet" to give 
mobile clients access to the pfSense LAN side.

Here is my problem: the setup *almost* works.  When I say almost I mean that 
mobile clients connecting from behind a NAT appear to have connectivity to the 
pfSense LAN but mobile clients not behind a NAT don't.

Here is an example: I have two test clients connecting.  One is a Mac desktop 
with direct Internet connection (wired ethernet using a public IP address) and 
the other is a Mac laptop connecting over WiFi (and a private IP address behind 
a NAT).  Both clients have identical client-side setups for the VPN in the 
networking section of System Preferences.  Both clients establish connections 
to the pfSense VPN without problem.  Tcpdump on the client side shows IPsec 
traffic being router over the respective WAN link.

If I ping a machine on the pfSense LAN side from each client I get a reply in 
the case of the Mac client behind the NAT but get "Request timeout for icmp_seq 
..." for the Mac client not behind the NAT.  Running "tcpdump -ni enc0 icmp" on 
the pfSense gateway shows ICMP echo requests incoming for both clients but only 
an outgoing ICMP echo reply response for the Mac client behind the NAT.  
Running tcpdump on the machine being pinged on the pfSense LAN I see ICMP echo 
requests and corresponding ICMP echo replies for both Mac clients.  I get the 
same when running tcpdump on the LAN interface of the pfSense gateway (i.e., I 
see matching ICMP echo request/reply crossing the LAN interface for each 
client).

So, it seems that ping requests are reaching the system on the pfSense LAN but 
the ping replies are only making it back out over the IPsec VPN tunnel to the 
Mac client that is behind the NAT.  The replies back to the client not using 
NAT-T appear to stop short at the pfSense gateway and are not encapsulated and 
sent over the IPsec tunnel.

I don't believe this is an issue of firewall rules because I would assume it 
would affect both clients in the IPsec virtual address pool.

Does anyone have any suggestions how I might get this working?  Does anyone 
have a working setup that is using the Apple "Cisco IPSec" client that is *not* 
operating from behind a NAT?

Any help is gratefully appreciated.

Cheers,

Paul.

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