When it worked.
If any security software is installed.
Think about any PRIVACY protection apps.
Is the popup noted at http://support.apple.com/kb/HT1418 occuring.
What error messages if any.
I have an iPad 2 and Outlook 2003. Outlook won't sync with my iPad..
However, they will sync on another computer. Then I can clear the iPad
calendar and then sync to main computer but the old calendar info syncs.
Outlook/ my computer seem to be holding on to the old calendar info in some kind of cache.