email message hangs in IIS smtp queue

By wstevison ·
I have a server that functions as a gateway email filter server running GFI Mail Essentials and Mail Security. Both GFI products have been confirmed as functioning correctly. Occasionally a message will get stuck in the SMTP queue. It will be delivered repeatedly and the receiving party on the outside will receive multiple copies until it is cleared from the queue manually. None of the hung messages have been inbound. When it happens it will cause some messages to perform the same way. Possibly 3 or 4 messages while other messages clear normally. I stop the SMTP service delete the messages that are stuck and restart the service.

It is a 2003 Standard Edition server with SP2 and all updates have been applied.

Any help would be greatly appriciated.

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