Missing Emails - where to start? 500 POINTS


We are using Exchange 2003 on our Small Business Server 2003. One of our users has complained that all emails from a particular email address have not been received. It is not a domain I am familiar with and is definately not on our blocked sender list/blacklist etc. I have checked the exchange server event log (I have enabled transport logs so can see when an attempt is made to deliver an email and if it succeeds), the anti-virus/anti-spam (Trend Micro Client/Server/Messaging Suite) engine running on the server and the Junk email folder on the users' PC - Cannot find anything! The other user does not receive a Non-Delivery-Report, so it seems as though the message is delivered, but I cant find any trace of it!

Some things worth mentioning:

-  The sending/receiving message size limits are quite generous, about 20MB I believe
- We are using the blacklist from Spamhaus in Connection Filtering
- We are using Sender, Recipient, Sender ID and Intelligent Message Filtering, but none of them have any entries. Sender ID is set to accept messages and IMF is set to reject messages with an SCL of 8 or more.
- anonymous access is checked in SMTP Virtual Server properties, as well as Basic Authentication, Require TLS authentication and Integrated Windows Authentication. The FQDN checks out OK and the server is setup to perform reverse DNS queries. We are using our ISP's DNS servers for this lookup, as we do for all internet traffic.
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GranModConnect With a Mentor Commented:
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is the exchange server  the MX for your domain ?

or any relay ?
5t34lth_G33kAuthor Commented:
Yes - the MX record points straight to our server. The only relays set up are the localhost address and its real, private address.
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Can the user prove these emails have not been delivered? Can the user prove that the emails were even sent?
Trying to troubleshoot message delivery when you are the recipient is very difficult, because until the messages hit your server, they are out of your control.

Message tracking is probably your best tool here. That will show you what Exchange is doing with the message.
Although in my experience most of these "missing" emails usually show up in another folder somewhere, often the deleted items.

try simulte the sending from outside with the same expiditor address (using outlook express and pop3 account, ou simulate smtp sending with telnet)

and see if the mail arrive ....

i have already seen a strange behaviour where sender mail server (real old server) was not "TCP" compatible with my customer server (exchange 2003)  ... but only one time....

can the expeditor try to send an email to you (postmaster @ ...) ?  
5t34lth_G33kAuthor Commented:
Sembee - I have looked into message tracking, but the emails do not appear here either.

I think you are right about it being very difficult. I have looked at everything I can think of and Im not really keen on spending much more time on this, since we cant even be sure the problem isnt with the sending server.
5t34lth_G33kAuthor Commented:
The user has since sent emails which have been received - I think we can put this one down to user error...
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