I have a user on outlook 2003 (11.8313.8324 sp3, exchange 2007 sp3) that when clicking send from a composed message the message doesn't send (confirmed through message tracking), and doesn't appear in sent mail. Sometimes the message will appear in her outbox in outlook along with radom other messages that haven't been sent, and sometimes the outbox appears blank in outlook. In OWA the outbox always contains the (93) messages that haven't been sent. They are not italicized or bold. They cannot be deleted or moved. When you open them in OWA they do not have a send button and have the message in a yellow bar "This mesage has not been sent". I've heard reports that this is a server side issue and upgrading to sp2 solved it for some, I upgraded to sp3 over the weekend and same behavior today. Is there a way to get these messages to send from the outbox? I have moved the mailbox to another DB and back which allows me to delete the messages, but the problem re-occurs and the user has to continually watch to see if the mail actually sends.

Hi Andrew, Have you made sure that you have ticked the radio button for encypted data between user and exchange server? You can find this under Tools, options, account settings. Cheers, Canadian Invasion

Is that known to cause this issue? I'll check that but the user is out today. I had since opened a case with MS and they had me delete their mailbox and create a new one, thought being that the mailbox was corrupted somehow. I'll be able to tell next week if that solves the issue.