Remove the stuck message in your Outbox by selecting File, Work Offline,
Delete.

"Don Smith" wrote:

Yes, I have checked the send mail immediatly box. I tried a repair on
office, it still didn't fix. I create emails, hit send and they stay
in my outbox (one is permanent and won't go away). To send them, I
close Outlook, then reopen and launch. Voila, they start sending
them. If I hit send/receive it says sending complete, but they are
still in my outbox.