Exchange 2003 Strange Email Problem

[tforeman]

Hello,

Been having a bit of a nightmare with our Exchange 2003 server. The story begins like this:

Over the last couple of weeks some emails sent to external recipients have not been arriving, not all of them just some randomly it seems.

When checking the exchange message tracking, it tells me that the message has been transferred to the appropriate server via SMTP.

So I thought I do some more checking to make sure, ran smtpdiag on the server, that came back all ok. Ran the online exchange connectivity tester, that was all ok. Ran a check to make sure our server wasn't blacklisted, nope that was fine too.

As a last resort I rebooted the server last night. When I came in the next morning I was greeted by several people asking why they had lots of NDR message's, some of them dating back to November. To my surprise the messages that the message tracking had told me were delivered had actually not been delivered! When I checked the message tracking again, the results contained some extra lines with yesterdays date duplicating the sending process again with a NDR at the end!

My questions are:

Does anyone have an idea what happened?
Why did the message tracking lie?
Is the any method to guarantee a notification to whether a message has been delivered or not as NDR's did not work on this occasion.

Tim

[AIT]

Is it worth checking that your ip isnt listed in some blacklist and therefore your emails are actually being deleted?

[tforeman]

Did a blacklist test that was fine. Emails weren't deleted, seem to be stuck in the exchange server but exchange had reported that they were sent.

[andydis]

do you use a smart host?

[tforeman]

No, we send emails directly.

[tforeman]

We are using Sophos Puremessage 3.0.1, so I am inclined to blame that for the messages getting stuck on the server and causing exchange to report incorrectly that the message was delivered.

The release notes for 3.0.2 mention a fix for messages getting stuck on the server.

[PiqueABoo]

Maybe, I've had no end of trouble with faulty Exchange-integrated AV scanning over the years (although some of it was MS's fault when they first introduced the APIs). My rule is that if you can get some external party to do the de-spamming & scanning then do.

[tforeman]

Any recommendations for third company solutions ?

[AIT]

Any recommendations for third company solutions ?

yes us ;-). Called MailScanner. A box dedicated to filtering spam and antivirus.

However i would still recommend Latest puremessage.

Microsoft ForFront Server is pritty nice aswell.

[bio]

Any recommendations for third company solutions ?

Barracuda Networks - Worldwide leader in email and Web security

bio..