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I will give a quick overview and then the details.

I have a Exchange 2003 environment that I have been asked to slap on a disclaimer on all outgoing mail. So I have setup a Windows 2003 server and put on the IIS 6.0 and setup the System with the GFI Mail essentials. Initially everything looks good. Though looking at the logs of the GFI I see that there are messages failing to be delivered.

There is not a lot of emails being bounced / NDR but I could see that there is also nothing getting back to the users. That is a bad thing since some of the messages are ones that previously could be delivered, and if I took out the relay server would be send quite fine.

So I have started to look at what items it could be. I did note that I had seen a article that you should try to set the HELO option (I had just seen this change today). I was wondering if there may be something else that I am missing? I am not seeing a pattern for these email but I can note that I can see that the.

The setup: Exchange server is setup as a back end Windows 2003 Server with WSUS and the IIS/SMTP relay setup. I had installed the GFI Mailesentials on this system for the Disclaimer option. Tested OK via telnet. both servers are stand alone servers in the same domain.

Exchange/email is not my strongest point so though it would be a good place to post. thanks

Thanks for any ideas?

share|improve this question
Look at the bounces. What do they state? And then did I get the setup right for outgoing mails?: IIS --> Exchange --> GFI --> Internet – mailq Sep 10 '11 at 7:56

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