Outlook E-mail is Stuck in the Outbox

When working with Microsoft Outlook 9 times out of 10 everything will work relatively smoothly. That 10th time, however, can cause Helpdesk and Windows Administrators headaches. One such headache occures when emails get stuck in the Outlook outbox. This is especially prevalent when dealing with secondary attached group mailboxes. Users will only become aware of this problem when they stop receiving responses to messages, meeting requests, or task requests. Often times they will also see the error "There are still e-mail messages in your Outbox. Would you like to exit anyway." when trying to exit Outlook.

NOTE:  Please make sure they are not in Work Offline mode, had a recent password change, that the Exchange Server is not connected for some reason. Antivirus must also be checked to verify that it is not blocking the email. 

First, make sure that Microsoft Outlook and Lync, if you use the service, is closed. 

Next,  go to control panel under the start menu. 

when presented with the Control Panel window arrange the "view by: category" by small icons in the upper right hand corner of the window. 

Next, select Mail

Click on "Show Profiles" 

Completely delete the Outlook Profile(s) 

Create a new profile under Control Panel, Mail (32-bit) by clicking the Add button and going through the Outlook wizard

Add any extra secondary group mailboxes in the same manner.
Reopen Outlook to make sure everything is now working OK. 

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