The next time this happens, check in the Project Email activity center to see if the email was actually filed. We have seen a situation where the email is properly handled by the server, but the Outlook client is out-of-sync with the Exchange server. The client thinks the email has not been filed when it actually has. We don’t know why this happens, and is perhaps a defect in Microsoft’s synchronization code.
Another way to tell if this has happened is to right-click on the folder in Outlook that has the items, choose Properties, and then click the Synchronization tab. If the server folder contains 0 items and the offline folder contains > 0 items, this is probably what has happened.
In Fifth Edition, you can fix this in two ways. One is to do what you did… uncheck Automated File Items in the Options dialog, click File Items (which really re-files the items), and then check Automated File Items again to turn it back on. This works fine for a small number of folders.
If you’ve got several folders with this problem, you might want to delete your .ost file and have Outlook re-generate it. It will get all new (and correct) information from Exchange when it re-builds itself.
In Sixth Edition, the File Items button will always file the items in addition to sync’ing the folders, as long as the server is not also working on your mailbox. This will make this process much easier, since you won’t have to disable and re-enable Automated File Items in the Options dialog.
Michael
