System cannot find the path specified when sending emails with attachments

Question

I've had an on going issue for some time on one of my clients whereby users will intermittently get this error "The System cannot find the path specified." when they try to send an email with an attachment.
The issue seems to arise generally (though reportedly not only when) when someone creates an email and attaches a file but leaves it for some time before finishing and sending.
The staff run in a Windows 2008 R2 full Terminal Server desktop environment on Office 2010 (32-bit 14.0.7140.5002) and several staff have reported the same issue.
I have been able to replicate the issue in their environment by creating an email and leaving it for some time.
After a fair bit of scouting around I found that if I monitor the temp directory that the attachments get placed into (content.outlook under Temporary Internet Files on user profile) and found that the directory with the attachments would disappear after
a period of time which would then cause the error where obviously Outlook could not find the file that had now gone.
I don't know of any Outlook settings that would cause this and the issue isn't related to temporary Internet files filling up as I've recreated the error on a user account where there is nothing else stored in the Temporary Internet Files.
To work around the issue I have changed the reg file that tells Outlook where to place these files (HKCU/Sofware/Microsoft/office/14.0/outlook/security - OutlookSecureTempFolder) to a location in the users home drive.
This appears to resolve the problem however I am noticing 1 issue with this.  Unlike the temp folder which gets purged after a file is no longer required, the location I've changed it to does not clear out old files.
While it shouldn't be too difficult to add a script that can clear the files at log off it would be good to see if anyone may know what the cause of the problem in the first place is.  I would rather it work as it should than have to bodge around changing
the folder and scripting file deletes.
Does anyone know of what maybe causing the attachments and content.outlook folder to disappear?
thanks

Answer 1

Do you have any redirected folder in your environment? Is the original Temporary Internet Files folder stored on a server?
Basically, the attachments remain in the Outlook Secure Temporary File folder if we exit Microsoft Outlook while email attachments are open. See:
http://support.microsoft.com/kb/817878
Flynn