I have Outlook 2007 on Windows 7 setup to send mail via gmail. I do this to archive the sent mail someplace searchable and off my computer. This works fine in Mail.app from my Mac and works some of the time from Outlook.
At some point it stops sending message. I have not noticed what causes this or even if it is something I am doing. I can connect to stmp.gmail.com with telnet, so I don't think it is a system or network issue.
Does anyone know a fix for this? Have others seen this strange behavior? Any suggestions for troubleshooting it?