Multi Site VPN setup w/ weird ping issue

[magik]

So I setup a multi site VPN but am having trouble pinging a specific machine from the central untangle router. Our setup is

Central Site --> North Site
--> East Site

With each site headed up by an Untangle router.

From a machine behind central I can ping this particular machine at the North Site and from within the North Site network I can ping the machine. But if I ssh into the central untangle router and try and ping the machine it hangs on the VPN route address. I can still ping other machines in the North Site network but this particular machine will not ping. Any ideas?

Route tables on the three sites are as follows (I sorted them to make them easier to read) Also note external IP addresses have been changed (ie. 1.2.3.4 & 5.6.7.8 & 9.0.1.2.3

I'm also wondering if my multi-site vpn is setup properly. I setup an address pool for each site in the advanced settings of OpenVPN. North is 172.16.102.1/24 and East is 172.16.100.1/24. In the Clients section of OpenVPN I set each local subnet to its respective custom address pool. Should they both be pointed at the same address pool?

Under Exported Hosts and Networks I have all three local LAN's listed (192.168.1.0/23, 192.168.61.0/23, 192.168.71.0/24)


Site-Center
172.16.100.0 172.16.102.2 255.255.255.0 UG 0 0 0 tun0
172.16.101.0 172.16.102.2 255.255.255.0 UG 0 0 0 tun0
172.16.102.0 172.16.102.2 255.255.255.0 UG 0 0 0 tun0
172.16.102.2 * 255.255.255.255 UH 0 0 0 tun0
192.0.2.0 * 255.255.255.0 U 0 0 0 dummy0
192.0.2.0 * 255.255.255.0 U 0 0 0 utun
192.168.0.0 * 255.255.254.0 U 0 0 0 eth1
192.168.60.0 172.16.102.2 255.255.254.0 UG 0 0 0 tun0
192.168.71.0 172.16.102.2 255.255.255.0 UG 0 0 0 tun0
1.2.3.4 * 255.255.255.240 U 0 0 0 eth0

Site-East
172.16.100.2 * 255.255.255.255 UH 0 0 0 tun0
172.16.102.1 172.16.100.2 255.255.255.255 UGH 0 0 0 tun0
192.0.2.0 * 255.255.255.0 U 0 0 0 dummy0
192.0.2.0 * 255.255.255.0 U 0 0 0 utun
192.168.0.0 172.16.100.2 255.255.254.0 UG 0 0 0 tun0
192.168.60.0 * 255.255.254.0 U 0 0 0 eth1
192.168.71.0 172.16.100.2 255.255.255.0 UG 0 0 0 tun0
5.6.7.8 * 255.255.255.248 U 0 0 0 eth0

Site-North
172.16.102.1 172.16.102.6 255.255.255.255 UGH 0 0 0 tun0
172.16.102.6 * 255.255.255.255 UH 0 0 0 tun0
192.0.2.0 * 255.255.255.0 U 0 0 0 dummy0
192.0.2.0 * 255.255.255.0 U 0 0 0 utun
192.168.0.0 172.16.102.6 255.255.254.0 UG 0 0 0 tun0
192.168.60.0 172.16.102.6 255.255.254.0 UG 0 0 0 tun0
192.168.71.0 * 255.255.255.0 U 0 0 0 eth5
9.0.1.2 * 255.255.255.248 U 0 0 0 eth0

[jcoffin]

I'm not clear. Which location is the hub of your VPN? Or are you daisy chaining? OpenVPN must have one Untangle as the master which the two satellite network connect to.

[magik]

Sorry. My Ascii art is a bit rusty. There is a central site that is the master. North and East connect as site clients