Your right ! I didn't state program. My apologies, trying to figure this puzzle out. We are using Outlook 2010 with an Exchange Server of 2010. I will check the archiving setup, typically we don't use it because we file our emails in Newforma. Email isn't stuck in Outbox, only one of the emails ended in drafts after the person couldn't find it in Sent Items he started re typing to send. the check box is set in Outlook 2010 for save messages to sent items. There is a Microsoft KB article with some other options.
http://support.microsoft.com/kb/2958272 . It is just really bizarre for some emails will file correctly and others won't show at all. They do go out, but this individual needs his sent items in order to track what has been said. I have checked the Track log explorer in Exchange Management Console and one of the weirdest things is that a message that was sent out to all employees, did go out, never went into his sent items but isn't tracked in the Exchange log tracker. I will be trying the solutions from the Microsoft KB and will let you know what happens.