Threat Management Gateway Reverse Proxy timing out.

Posted on 2011-04-27
Last Modified: 2012-06-27
Hi Guys,

we have a newly installed Threat Management Gateway which I have installed on a Server 2008 R2 VM (running on ESXi 4.0).

I have setup a reverse proxy configuration with one network adapter on this machine.

It has been configured with an internal address and a default gateway of our firewall/router.

This firewall/router has a route to pass all outgoing traffic to the ADSL router (fibre's not been installed yet), it also has a firewall rule to pass all port 80 traffic to the TMG.

I would like to setup this TMG server to become a reverse proxy so that people can access the multiple web applications we have hosted in house.

Currently I have setup only one firewall rule which I have pointing to our sharepoint server.

Everytime I try to make a connection to this sharepoint server it times out (as shown by the logs, error below).

It has worked ONCE but not again, I first thought this may be an issue with the firewall rule but I am now beginning to think it may be a networking/routing issue, as the TMG server is definitely getting the connection, but something is happening during the communication with the server and client which is causing the connection to time out.

In addition to that everytime there is some funky stuff going on with the network adapter - from time to time it's going up and down - sometimes we can't ping any servers, sometimes we can.

Everytime I try to go to the site in question directly from the TMG server it self it works - so that makes me think that there is a configuration issue with TMG itself.

Thanks for reading.
Failed Connection Attempt HL-CORUSCANT 28/04/2011 3:03:23 p.m. 
Log type: Web Proxy (Reverse) 
Status: 10060 A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond.  
Rule: techdocs 
Source: Internal ( 
Destination: Local Host ( 
Request: GET 
Filter information: Req ID: 09bc9650; Compression: client=Yes, server=No, compress rate=0% decompress rate=0% 
Protocol: http 
User: anonymous

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Question by:lemonville
    LVL 31

    Expert Comment

    what about a web chaining rule?
    LVL 1

    Accepted Solution

    The default gateway of the recipient server had not been set to the reverse proxy
    LVL 1

    Author Closing Comment

    This is the answer

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