Microsoft Outlook Connector will not sync deleted messages. Deleting messages in Microsoft Outlook will not delete these messages from your Hotmail/Live Mail web interface. Windows Live Support will direct you to the Microsoft Outlook Connector Support team. There is no solution for this. Perhaps a new version of Outlook Connector will finally fix this. Until then I found a work-around that is not clean, but it works.
1. Manage folders in Windows Live Mail
2. Create a New Folder
3. Name it how you want
4. When using Microsoft Outlook “Move to Folder” instead of deleting
5. Back in Windows Live Mail you can delete the folder.
While this in no way is a clean solution it is faster than the alternative of deleting all the messages a second time after Outlook Connector does not synchronize them. If you are moving email to say a Gmail account you will have to copy them to your Gmail account instead then move them to your temp delete folder.
Know a better solution? Share it in the comments.
