external recipient intermittently unable to send email

Posted on 2007-10-19
Last Modified: 2013-11-30
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?

Question by:pteeter
    LVL 4

    Accepted Solution

    If there are no SMTP log entries for the messages that do not get through, then it si definetly not your mail server. Even if the message fails or is not delivered, the SMTP logs will show the attempted connection and email delivery.

    Also, is the client getting a Failed Delivery message back? This should happen automatically. Most mail servers have automated Delivery Status Notification, and either your mail server or their mail server should notify the sender that the message cannot be delivered.


    Author Comment

    I totally agree.  If i see no trace in my logs, then it ain't getting to my server's only partly my problem.

    I think initially the client was getting some kind of NDR message.  Here's the only NDR I have seen regarding these issues:

    Sent: Tuesday, October 02, 2007 3:36 PM
    To: Client Username
    Subject: failure notice

    Hi. This is the qmail-send program at
    I'm afraid I wasn't able to deliver your message to the following
    This is a permanent error; I've given up. Sorry it didn't work out.

    preline: fatal: unable to run procmail: file does not exist

    --- Below this line is a copy of the message.

    I also see from reviewing previous messages in this thread that our client is using GFI to filter spam.

    Still no word from the client or their mail admin to further trouble shoot the issue.

    LVL 4

    Expert Comment

    I am assuming this NDR message came from your clients own mail servers.
    Looking at their logs would probably help resolve this issue pretty quickly,
    but if you are not getting any cooperation, you may be spinning your wheels

    If you have the cooperation of the client, but not their support team, your only
    option is to have the client send out some test emails, and see what comes
    through, and what does not.

    Have the client send several emails to your server to a few different email addresses,
    including the address. Make sure that the client
    is typing in the recipient email manually every time, and not allowing Outlook to
    AutoFill the recipients.  

    Author Comment

    Yup, been trying to get in touch with someone who has access to the SMTP logs.

    Thing is, politically, it may not be possible to get the client to do that kind of manual testing.  We'll see.

    By-passing Outlook AutoFilling the address is the key, I think.  We'll certainly try it, though looks like it will have to be Monday as client is in MDT and we're PDT.

    LVL 4

    Expert Comment

    I hate it when politics get in the way of tech support.. :)

    Best of luck.

    Author Comment

    LVL 104

    Expert Comment

    As the recipient there is little that you can do.
    The senders need to prove that the message is being delivered to your server and then rejected (or not). Until the message is delivered to your server there is nothing that you can do.
    The headers in the client will not really help, what you need is the SMTP logs (or they need to look at them). Message tracking may show what is happening to the message as well if the other server is Exchange.


    If your question has been answered, please remember to accept the answer and close the question.

    Author Comment

    Thank you for re-affirming what I was pretty sure I knew to be the case.

    I'll keep working on our client to provide logs.


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