Existing users, 
iPhone fails to sync all contacts; iTunes hangs on “Syncing contacts”
Posted 1 July 2007 @ 8am in Troubleshooting
Several users have reported an issue where iTunes fails to properly synchronize contacts with the iPhone, hanging repeatedly at the “Syncing contacts” phase.
It appears that in most cases, this issue has to do with individual contact entries that contain problematic data. For instance, some users have reported that the issue started after photos were added to contacts on the iPhone.
Try creating a smaller group of contacts in your chosen application (Mac OS X Address Book, Entourage, Outlook, etc.) and re-attempt synchronization. If it works, add a few more contacts in batches and continue to re-attempt synchronization until the problematic entries can be isolated.
Feedback? info@iphoneatlas.com.
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Posted by Fierce Bob
1 July 2007 @ 3pm
Just discovered something interesting about the iPhone’s ability to sync with Entourage on the Mac.
I was looking through my Contacts list on the phone, setting up favorites, and found that many names seemed to be missing. Turns out that the iPhone was syncing only with the Mac Address Book and iCal programs. Because most of my contacts had been transferred when I first synced the phone, I thought it had just automatically discovered that I used Entourage. But no. Upon investigation, I realized that at some point I had imported my Entourage contacts into Address Book, and the iPhone was just syncing to that. So the data was pretty old.
But there’s good news.
You can, indeed, get the iPhone to sync both calendars and contacts with Entourage. It’s just a little convoluted to set up, and not documented on Apple’s iPhone pages (yet). At least it’s not documented anywhere I could find it.
To do this you have to first setup Sync Services within Entourage. (Sync Services only became available with the 11.2.3 update to Entourage, so if you’re using an earlier version, you won’t have it.) Once you setup Sync Services, Entourage will automatically synchronize your Contacts and Calendar events with Address Book and iCal, respectively. Then the iPhone will sync to Address Book and iCal, and all will be well.
I spoke to a guy at the Genius Bar about the Entourage calendar sync yesterday, and he didn’t know what I’ve just written here. I imagine a number of people are going to come up against this in the next few days, and I would expect the documentation on Apple’s site to be updated with the necessary information.