No idea what happened, but found that Outlook wouldn’t send anymore messages via GMAIL IMAP. I found this little morsel and viola… problem fixed.
- Exit out of Outlook 2003 on the machine with the issue
- Open the registry (Start->Run->type cmd->click Ok)
- Navigate and open the following registry key HKEY_CURRENT_USER\Software\Microsoft\Office\11.0\Outlook\Security\OutlookSecureTempFolder
- Within the key…it should say something like %USERPROFILE%\Local Settings\Temporary Internet Files\OLK3D\
- Highlight and delete %USERPROFILE%\Local Settings\Temporary Internet Files\OLK3D\
- Close out of the registry and open Outlook 2003!