Problem emailing pictures taken on iPhone

Question

I have what looks like a double fault problem with emailing pictures taken on the iPhone that I hope someone can help me resolve.
A user reported to me that he cannot email pics taken on the his iPhone and also has trouble forwarding emails with attachments, including .Doc files.
I took his iPhone and mine (both 3gs with iOS 4.0.1) and set up his account on my iPhone and a test account on his iPhone. Both his account on my iPhone and the test account on his iPhone could not email a picture taken on the phone except in the smallest size. The larger size messages just sit in the outbox through repeated send/receive operations.
However, with my account restored to my iPhone I can send the same picture used in the test at the largest size.
I tried a network reset on the user's iPhone without changing the outcome. As part of my procedure I also power-cycled both phones after deleting email accounts before adding new ones.
Other things to know: I've rebuilt all the Exchange 2003 virtual directories and done other server troubleshooting for other iPhone problems and am confident the various permissions and other settings are correct. We have about five iPhone users and no other user has reported this problem. However, a couple of users need to have "days to sync" set to "no limit" or I get large numbers of HTTP 500 event log errors. Other users have "days to sync" at the default setting with no problems.
Has anyone else encountered the scenario I've described and been able to resolve it?

Answer 1

Here is the fix that fixed the fix we were in (thank you Microsoft!):
We need to ensure the permissions on the %temp% folder on all your Exchange servers (Both FE and the problematic BE) are set as below:
- System - Allow Full Control
- Authenticated users - Allow Read & Execute , List Folder Contents , and Write
"System" was listed but not "Authenticated Users". Right after I added it I got a message that someone's iPhone had been trying to send me for over a month.