The Endless Battle With Iphone Syncing

Question

I've been having nothing but problems syncing my reasonably new iPhone with my contacts. When I first got it, I immediately entered contact info into the iPhone itself.
I put in some numbers, some names, a couple pictures for my contacts. Then when I first synced the phone, I got an error message that iTunes couldn't sync the phone with my contacts because an error occurred while merging data.
Through some experimentation, I found that I could sync the iPhone to my addressbook as long as there were no pictures in the contacts. If I tried to put a picture in a contact on the computer, it just wouldn't transfer to the phone. If I tried to put a picture on the phone, I would get an error message when trying to sync to the computer.
I tried all of the regular fixes, i.e. resetting iSync, reinstalling iTunes, trashing and rebuilding AddressBook. Nothing seemed to work. Fed up, I completely reinstalled Mac OS from my restore discs. After a lot of work and trouble, I finally had my iPhone syncing contacts back and forth with my computer, including pictures. For a week.
Until last night.
For some inexplicable reason, it just stopped. I plugged in my phone to sync, went to do something, and came back to see the dreaded popup error message about not being able to merge data. So my first instinct was to use the option to replace the contacts on the phone with the ones on the computer. In a terrible turn of events, all that did was completely erase every contact on my phone. So at this point I can't even tell who's calling me or who I'm calling without looking up their number on my computer's addressbook.
As an experiment, I made a dummy contact entry on the phone with a gibberish name and synced the phone. The contacts on the phone and computer stayed the same. I deleted the contact on the phone, and again synced to the computer using the 'replace all' option. It came back. The gibberish entry came back to my phone after I deleted it. Is it saved somewhere on my computer? Is there some secret addressbook list other than the information stored in /Library/Application Support/Address Book that iTunes ACTUALLY syncs to? I'm at my wits end here. I just want a phone that will WORK without me living in fear of doing destructive restores on my computer every week.
God, if ANYONE could help me with this it would be miraculous. I haven't found any reports of problems exactly like this, but I've found some that are similar. As I said, I tried the usual remedies like resetting iSync preferences and reinstalling iTunes, but I can't get anything to work. I've restored my phone probably a dozen times and my computer half as much. This is frustrating to no end.
-Adam

Answer 1

I too have been fighting the same issues. Sometimes synch works and sometimes it doesn't. It is an endless process - the synch function can run for hours and never complete. I have re-installed iTunes dozens of times and have spent - to date - over 32 hours on the phone with apple support - I have two product specialists looking into it. The first three phone folks basically could do nothing - one even suggested that iPhones will not synch with Outlook 2003....the product specialists have been unable to help. I have replaced t he phone thru a warranty exchange at the store - and still nothing. When it does work it's great and then I dont synch for a day or two it loses all connectivity and will not synch. I also canot ustilize exchange....it will not recognize our network and I have had some of the best IT folks in the country try to synch it to an exchange server. I have a number of friends having the same issues - Apple has really dropped the ball on this one....it's back to a Blackberry for me.