There is no easy way to describe this, so I'll just start. I am running a Snort IDS/FW with 4 interfaces, but we'll just be concerned with 2 (eth0 and eth2 + ipsec0). Ipsec is functioning, so that is not the problem. Local subnet 10.10.41.0/24 Local GW 10.10.41.100 Remote Network: Network 111.111.0.0/16 Eth0 111.111.3.160 (gw 111.111.3.129) Eth2 111.111.3.163 Add. Route route add 111.111.8.204 gw 111.111.3.129 dev eth2 (just cause I want to ensure it goes out eth2) and I can ping that host; it does go out eth2 To ensure that there is no unintentional DROPping of packets there are only 3 rules: iptables -A POSTROUTING -t nat -o ipsec0 -s 111.111.3.160 -d 10.10.41.0/24 -j SNAT --to 111.111.3.163 iptables -A POSTROUTING -t nat -o eth2 -s 10.10.41.0/24 -j SNAT --to 111.111.3.163 Iptables -A FORWARD -j ACCEPT Basically, I want to send a packet through the tunnel (ipsec0) and out to system 111.111.8.204. Because the packet will arrive as source 10.10.41.100, and I cannot control the route table of system 111.111.8.204, I figured I would SNAT the packet from 10.10.41.100 to 111.111.3.163. If I do a tcpdump on ipsec0 I see the pachet coming in: (Remote Side - Inbound) tcpdump -i ipsec0 -p -n -nn icmp 13:27:33.916290 10.10.41.100 > 111.111.8.204: icmp: echo request (DF) 13:27:34.919120 10.10.41.100 > 111.111.8.204: icmp: echo request (DF) 13:27:35.931122 10.10.41.100 > 111.111.8.204: icmp: echo request (DF) 13:27:36.923962 10.10.41.100 > 111.111.8.204: icmp: echo request (DF) However, (On the remote side) "tcpdump -i eth2 -p -n -nn icmp" or "tcpdump -i eth0 -p -n -nn icmp" (just in case) do not show any packets outbound (to 111.111.8.204). I can't see anything wrong with my rules, but sometimes I can't think outside the box.....any ideas? Thanks, Andy To verify the tunnel works: [root@xxxxxxxx root]# ping 111.111.3.163 PING 111.111.3.163 (111.111.3.163) from 68.68.130.209 : 56(84) bytes of data. 64 bytes from 111.111.3.163: icmp_seq=1 ttl=64 time=29.5 ms 64 bytes from 111.111.3.163: icmp_seq=2 ttl=64 time=31.7 ms 64 bytes from 111.111.3.163: icmp_seq=3 ttl=64 time=26.1 ms 64 bytes from 111.111.3.163: icmp_seq=4 ttl=64 time=26.7 ms [root@xxxxxxx root]# tcpdump -i ipsec0 -p -n -nn icmp 13:35:50.883841 10.10.41.100 > 111.111.3.163: icmp: echo request (DF) 13:35:50.884001 111.111.3.163 > 10.10.41.100: icmp: echo reply 13:35:51.832915 10.10.41.100 > 111.111.3.163: icmp: echo request (DF) 13:35:51.832976 111.111.3.163 > 10.10.41.100: icmp: echo reply 13:35:52.847691 10.10.41.100 > 111.111.3.163: icmp: echo request (DF) 13:35:52.847749 111.111.3.163 > 10.10.41.100: icmp: echo reply 13:35:53.859624 10.10.41.100 > 111.111.3.163: icmp: echo request (DF) 13:35:53.859684 111.111.3.163 > 10.10.41.100: icmp: echo reply