I have a mail server run on Exchange 2003 Service Pack 2, on a Microsoft Server 2003 32bit. I am having a issue when some messages are getting stuck in the outbound queue. This issue is very intermittent, and only happens to messages that are leaving the organization. The organization is email security solution provided my McAfee Saas to secure incoming filter out spam, and check all emails that are going outbound and encrypt any emails that are going outbound.
There is a SMTP Connector setup to McAfee Saas to forward all emails through their system and send it out our behalf.
When I check the queues, I seem some messages stuck in a retry. When I look up the message in Message tracking center, it looks like the system never tried to trigger the final hop. I have contacted McAfee and they are not seeing any history of the messages coming to their end. It look like the message never leaves the system.
I attached a sample screenshot of to emails that were tracked one was successfully sent and the other was not. Both emails were sent by the same user and sent to the same recipient.
The issue is intermittent not all messages are getting stuck only some, and appears to be be random.