Trouble syncing iPhone & Address Book? Try this.
If your Address Book won't sync to your iPhone over me.com, even when you've done everything the Apple Tech folks say your should do to fix it, the chances are the problem is that one or more of the email addresses in your Address Book are corrupted. As soon as these are found and the data is re-typed onto a replacement card and the corrupted originals deleted, the syncing problem usually goes away. The trick is -- how to find the corrupted email files in Address Book?
Here's what I did: it took a bit of time but now it's working just fine. It turns out I had 4 corrupted email addresses among the 730 I have in my Address Book.
Open up Address Book and make a new "Group" -- call it something convenient like Test 1.
Select the first half of the entries in your "name" list and drag them into the Test 1 group.
Open Mac Mail and in "Preferences - Composing" select "When sending to a group, show all member addresses".
With this selected, if you type a group's name in the "to" or "cc" field in Mail all the addresses should appear there -- that is, if the group has no corrupted addresses.
If the addresses don't automatically appear, and you need to delete the group name manually from the blank email, there likely is something wrong with the addresses in that group. This is where the "Test 1" group comes into play.
Open a new blank email, and type the name of the group you just created in the "to" line. If all the addresses appear, then there is nothing wrong with the first half of your list of email addresses.
Delete the addresses from the group (just from the group... not the Address Book), and replace them with the second half of your list of email addresses. If you enter that group name in the "to" or "cc" space in a blank email chances are that all the addresses will not appear. That shows that the corrupted email address is somewhere in the second half of your list of email addresses.
Delete the bottom half of the email addresses from the group, and try again to enter the group in a blank email. If the addresses appear, you know that the problem is in the bottom quarter of the address list, the ones you deleted. Continue adding or deleting batches of email addresses until you find the one (or more than one as in my case) that is hanging up the appearance of the email addresses in the email.
Fixing corrupted email addresses:
When you find the name that is causing problems you can create a new address card and enter the name, phone number and email address, etc. that is on the corrupted file. You need to re-type the information, simply doing copy and paste from one card to the other does not seem to remove the cause of corruption of the file. When done, delete the original (corrupted) file and see if the expanding address works when you type the group name in the address line of a blank email. You can create another group to test the single address: slide the new name into the group, and then see what happens when you enter that group name in the address line of a blank email. If the group name expands properly it's a sign the address is no longer corrupted.
It took me a while to find the 4 corrupted email address files in my Address Book... time well spent, I say: I really rely on proper syncing using me.com when I'm working and away from my computer. I enter information about new contacts in my iPhone and the new information appears on all my synced devices.
Hope this works
cheers
