I've had this problem since OL2000 and now on 2002. I'm using OL2002 in IMO mode. Connected to a T1. If I have it set to "send immediately" often, hitting CTRL-ENTER when finishing a message, the mail stays in the outbox with a "this message has not been sent" on it. There's also a "mail delivery error" in the status bar. A simple click on the SEND button then sends it off. Often, the recipients claim they've gotten the email twice.
This has happened on different accounts (though I'm only using one now) and different SMTP servers.
It doesn't happen if I disable "send immediately." I'd like to "send immediately" without having the mail just sit there. What's up here?