I hate it when this kind of thing happens. :)

http://www.howto-outlook.com/Faq/messagestuckinoutbox.htm might lead you down a 
path that will help.

From: Chris Blair [mailto:chris_bl...@identisys.com]
Sent: Thursday, January 20, 2011 2:24 PM
To: MS-Exchange Admin Issues
Subject: RE: Emails in Outbox

Yes. They remain in the Outbox. We can manually move them or delete them.



From: Missy Koslosky [mailto:mi...@notsoclever.com]
Sent: Thursday, January 20, 2011 12:57 PM
To: MS-Exchange Admin Issues
Subject: RE: Emails in Outbox

Have you tried having them restart Outlook?

From: Chris Blair [mailto:chris_bl...@identisys.com]
Sent: Thursday, January 20, 2011 1:43 PM
To: MS-Exchange Admin Issues
Subject: Emails in Outbox

Running Exchange 2007, Sp3 HF2. Have a few users getting emails stuck in the 
Outbox. I checked the logs, and the emails are being sent, but they are not 
moved into the Sent folder.

The Outlook profiles are all non-cached, and running 2007, with latest SP and 
updates.



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