I am using Outlook 2007 and exchange server. When send emails they oftentimes get stuck in the Outbox with a sent date of "None". If I restart outlook and try resending the messages, they will oftentimes go out. I am having to restart outlook 5 times a day right now. Any ideas what would cause emails going out through exchange server to just "get stuck"? Sometimes when I sent the emails and I watch the Outbox folder, the messages will appear in the outbox with a "sent" date, then after a second or so that "Sent" date will just change to "none" and the email just won't go out. Any advice on how to troubleshoot or fix?
One other note...some messages just NEVER go out 9regardless of how many times I hit restart outlook and hit send) and I need to rewrite them by creating a new message and sending and that new message.
NOTE: this appears to happen when I'm in a state where I am "Connected to Microsoft Exchange".