Outlook calendar sync issue with iphone

A friend has a desktop running XP with Outlook 2003, iTunes 10, an iPhone 3G running iOS4.
In Outlook, he has his personal contacts and calendar, both with lots of entries.
iTunes is configured to sync his contacts and calendar to his iPhone.
The contacts sync successfully - the calendar does not, meaning the calendar on his iPhone is completely blank, no entries.
We tried resetting the sync history in iTunes, creating a test appointment on both the iPhone and Outlook - nothing.
We then set up a temporary local user on the XP box, configured Outlook, launched iTunes and went to configure calendar syncing when we noticed something different.
When logged in as the temp local user account, in iTunes > iPhone > Info > Sync calendars where you have the choice between All or Selected calendars, under Selected, there was a selectable line item called Calendar.
However, when we switched back to the regular domain user account, that line item was not there.
This leads me to believe that iTunes in that domain user profile for some reason does not detect Outlook calendar, yet it does as the local user.
I thought maybe it has something to do with the user role (he was member of some custom group, not sure what the exact permissions are) and changed him to an administrator role, logged out/back in, tried again, but no difference.
I am not sure how to further troubleshoot this. What can I try to make iTunes detect the calendar? It's really puzzling because it sees the contacts in Outlook and syncs them just fine.
Any suggestions would be appreciated.

This sounds just like the problem I am having since downloading the latest version of i-Tunes. Initially i-tunes wasn't recognised so after reinstalling i-Tunes and it's 5 other associated programmes I found that there was a cmpatability isuue (Right click i-tunes icon and go to compatability tag) Once this was sorted my Outlook calendar would not sync with my i-phone. 2 weeks later I am told it is because I have Outlook 2002 and need to upgrade. Frustrating as it worked ok before the latest upgrade.

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