Outlook 2003 Outbox Messages Will Not Send Or Delete...

The Solution:

Within Outlook Express go to Tools > Send/Receive > Send/Receive Settings > Define Send/Receive Group... Ctrl+Alt+S. Then in the "Send/Receive Settings - All Accounts" dialog box click Account Properties and the "Internet E-mail Settings" dialog box will come up. Click the Advanced tab then move the Server Timeouts slider to "Long 10 minutes". Click OK then OK then Close to close out of the dialog boxes and try to Send/Receive your email. Since the server will have more time to send the mail, those big emails might make it. If they make it (or do not make it) when sending is done, you should be able to delete the Outbox messages or perhaps move them, at least we could which saved the day.

"The outbox had two 29mb messages that could not be deleted. I finally found deep within the Internet Email settings the Server Timeouts. I set it to 10 minutes and one message sent and the other did not. But now that it did not send, I could now delete the second message and move on with my life!"

The Logic:

With all of our searching we never did find the solution. We were very happy to have figured this out though and share with others the solution. The evidence seemed to point to Outlook thinking that is was still sending the messages. It did not matter if we were connected or not, working offline or not, the error messages seemed to indicate Outlook thought it was sending. "Outlook has already started sending this message" or something close to that wording, was the error message. We thought if we could allow the message to send and succeed or actually fail, then Outlook would stop thinking it was still sending. By increasing the server timeout and giving the program the time it needed is what helped.

Other Ideas:

Another suggestion is to increase the speed of your connection if you can. Adjust your antenna or move closer if you are wireless or perhaps Cat5 right into the router if that is an option.

Be aware you need to NOT be in "Work Offline" mode for messages to send in some cases. File > Work offline.