external recipient intermittently unable to send email
Posted on 2007-10-19
One of clients is having intermittent, non-reproducible problems sending emails to my domain. Message A to one recipient will go through no problem. Message B, sent literally 3 minutes later, to the same recipient will fail. Our SMTP logs show a typical dialog for Message A but no log entries at all for Message B.
Our client has had her desktop support admin clean out her GAL, PAB, etc. She even had Outlook uninstalled and re-installed.
Early on on the troubleshooting process, her desktop support admin forwarded me a message in which the address she was using for one of our recipients had our domain name *pre-pended* to the username portion of the email address. Like this:
Seeing this made me think it was definitely operator error, the client simply somehow got the wrong email address.
I am now seeing that messages that fail to get to us have a To line (in messages that have been forwarded to me) that resembles:
To: 'User Name'
Notice the single quotes. Whereas messages that do make it through to us have a To line that resembles:
To: User Name
Notice the lack of single quotes.
I'm unable to obtain ample header information so that I can see to what address our client is actually addressing these messages.
Since the failed messages don't appear to make it to our mail server, I still believe that it's operator error on our client's part but they firmly believe the problem lies in our mail server. I have tried to get their desktop admin to escalate the issue to his email administrator, so far no luck. I'm thinking I really need to have someone parse their SMTP logs to see if the messages are being sent and if so to what address.
Can someone advise me how best to get my client to export a sent message so I can view the header information and figure out where she is really sending the message? What's the best method for doing this in Outlook 2007?
Any other thoughts on how to figure this issue out?