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Exchange failing to send to all recipients (error Numeric Code: 4.4.7)

I have a user who frequently sends emails to members of a project team, three on our local domain, and three on a customer domain.  periodically, we get a "delivery delay" error Numeric Code: 4.4.7.

When I looked into this with the MS exchange message tracking center, I found that the local domain recipients delivered ok, and one of the remote recipients was delivered, but the other two are failing.  The tracking center shows the following:

SMTP: Started Outbound Transfer of Message
Message transferred to clientdomain.com through SMTP
SMTP: Started Outbound Transfer of Message
Message transferred to clientdomain.com through SMTP
SMTP: Started Outbound Transfer of Message
Message transferred to clientdomain.com through SMTP

This continues ad infinitum.

I noticed that a "good" message ends with the entry: Message transferred to clientdomain.com through SMTP and does not continue.  What could be causing this delay?  Note that during this delay period, other mail is going back and forth successfully between the domains, so it seems to be something about this message. And to repeat, one of the three far end recipients actually got the message.  This is quirky enough to sound like a bug.  Help?

If it helps, we are using Exchange 2003 on Server 2003.  The far end server announces itself as Microsoft ESMTP version 5 (we are version 6)

Thanks --Dale




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dvanaken
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dvanaken
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SembeeCommented:
This would appear to be a fault with the remote site.
Can you send an email message to each recipient separately? If so, then it would appear that the remote site is taking exception to your message coming in to more than one address. Probably overzealous spam filtering.

Simon.
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dvanakenAuthor Commented:
Simon, thanks.  Unfortunately, that means I can't fix it!  Can you help me understand why spam filtering would cause the repeated cycle of "message transferred" that I saw in the log?  --Dale
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SembeeCommented:
You can't fix it because the problem is at the other end.
Their spam filtering application is probably refusing the connection, but not sending back a fatal failure. It is probably sending back a temporary failure (ie try again later) or dropping the connection in such a way that the Exchange server thinks that something has gone wrong - it then tries again.

Simon.
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dvanakenAuthor Commented:
Another user just had the same problem with mail going to another recipient domain entirely - and this just had one recipient - two tries, a day apart - each ended up showing the same behavior - the contast "looping" as shown in the tracking center.  As long as you feel that this cannot be on my end, I'll forget about it, but I'd like to be able to get mail through to this second guy.  By the way, both emails that showed failures had either a dot or underscore in the recipient's email address - mean anything?

--Dale
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SembeeCommented:
Both a dot and underscore are valid characters for email, so that will not be an issue. If you are having problems with getting email delivered to certain domains, then what I usually suggest is to create an SMTP Connector to send email through your ISPs domain, then add domains you have problems with to this list.
http://www.amset.info/exchange/smtp-connector.asp

Simon.
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dvanakenAuthor Commented:
Simon, once again, you are a fountain of information - thanks and best regards. --Dale
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