We are using Microsoft Exchange 2003 sp2 (front end server and mail server) with our Clients running Outlook 2003 in Cache mode. Some users are having the most bizarre random problem.
From their desktops, users will either reply to an e-mail or create a e-mail from scratch and click send. While the users believe the e-mail went to it's destination, the message does not show up in their sent items, and is not stuck in the Outbox. When I get a call about the issue, I can connect to Outlook Web Access, and there will be a handful of e-mails in their Outbox (which does not show up in cache mode), and some of which are months old. If I connect directly to their mailbox not using cache mode, the same handful of messages will be in their Outbox, and then they will send. These users don't even use OWA, so I know that isn't a variable.
Now I have users who need to reply to a handful of people as to why an e-mail they thought went out 2 months ago went out 5 minutes ago!
If anyone has any thoughts as to why this happened, or how I would be able to tell what other mailboxes are affected, or how to stop this from occuring again, it would be greatly appreciate!!!