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TMG Traffic For a Specific IP isn't leaving the server despite valid routes and no firewall

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Hi,

 I'm struggling to troubleshoot a TMG networking issue:

I have a TMG server setup in my DMZ. Inbound traffic hits the a 3rd party firewall router, goes to the TMG server and is then routed back through the 3rd party firewall router to my internal network. I've setup web publishing rules and listeners for IIS sites and SMTP traffic using a different IP to listen for 2 different websites and another IP for SMTP.

The issue I have is that my TMG server can't ping a server on the internal network on a specific IP:

TMG can ping 192.168.11.190
TMG cannot ping 192.168.11.191

Firewall rules are configured to permit traffic (no deny connections are shown in the monitor).

tracert and pings to 192.168.11.190 hit the internal IP of the 3rd party router
tracert to 192.168.11.191 simply responds with * * * * before timing out

Monitoring from within TMG shows the correct IP is being used in both cases (internal NIC 192.168.10.10).

A route print from TMG has a valid route to the internal network:

(network)192.168.11.128 (mask) 255.255.255.128 (gateway) 192.168.10.126

In summary:
 - TMG can ping 192.168.11.190, but not 192.168.11.191
 - Valid routes exists 
 - No firewall rules are blocking communication
 - Traffic to 192.168.11.191 doesn't seem to be leaving the TMG server 

Any advice on solving this would be appreciated.

Cheers

 



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