Windows 2003 SBS Mail stuck in Remote Destination queues

35 pts.
Microsoft Exchange 2003
SBS 2003
We are a church and we have a Windows 2003 R2(Sp2)SBS with Exchange. We continually get email stuck in the Remote Destination queue. They will eventually go to a retry state but never get sent. We can receive incoming mail. Rebooting the server generally releases them. We do have a newsletter that sends 150 emails at the same time. Most of these are sent, but about 10% get stuck. The error logs have several of these messages "This is an SMTP protocol log for virtual server ID 1, connection #25. The client at "" sent a "helo" command, and the SMTP server responded with "501 5.5.4 Invalid Address ". The full command sent was "helo H<5". This will probably cause the connection to fail." What does this mean? How do you correct it? Is this the root cause? This has been driving us nuts and we have to keep rebooting the server to get the email sent. Any help would be greatly appreciated. Thanks in Advance!

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Since you have only about 10% of these stuck, i’d say this is normal. This means that the recepients email address wasn’t found. It could have been either a typo or a problem at the receiving end.

You can test if these are good emails or not by emailing from a third-party email service like yahoo mail or gmail to the failed address.

Sounds like there might be a Cisco firewall in play here, try toggling the SMTPfixup portion of your cisco firewall, if you have one… sometimes this gets in the way.

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  • CHEF
    Thanks for your feedback. The emails are valid addresses. If we reboot the server or unload the SMTP service, they are sent. Its like they get stuck and never retried. We have loaded all OS and Exchange 2003 updates that I'm aware of. A virus scan indicates no infections. Unloading the SMTP service will sometimes give an "unresponsive" error but it does seem to unload. This is driving us nuts! Any help in resolving this would REALLY be apprciated.
    35 pointsBadges:
  • Jerry Lees
    Sounds like maybe we might need to know the SMTP retry interval settings for your SMTP connector, Can you share these?
    5,335 pointsBadges:

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