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OS X Address Book contacts not syncing with iPhone #

mont3's instructions from 2008 helped us resolve a local (USB) Address Book sync issue. I have fixed a number of typographical and procedural errors (including the potentially tragic instructions to "Go to FINDER, LIBRARY, APPLICATION SUPPORT and delete everything in there") and updated the process for Snow Leopard:
  1. Backup. Backup. Backup.
  2. Export all contacts from the OS X Address Book as a vCard (attempting to use an Address Book Archive instead did not resolve the sync issue). Note that groups are lost during this process.
  3. Delete all contacts and groups from the OS X Address Book and then quit Address Book.
  4. Delete ~/Library/Caches/com.apple.Address Book
  5. Delete ~/Library/Preferences/com.apple.AddressBook.*
  6. Delete all files and folders inside of ~/Library/Application Support/AddressBook. Note that images are lost during this process. See mont3's original post for information on saving them first.
  7. Open /Applications/iSync.app and click iSync > Preferences > Reset Sync History... Reset Sync History.
  8. Import the vCard containing all of your contacts into Address Book.
  9. While holding the Command and Option keys (to prevent auto sync), plug in your iPhone. If "iTunes is running in safe mode" message appears, click "Continue" while continuing to hold the Command and Option keys.
  10. Click the iPhone icon under "Devices" and then click the "Info" tab.
  11. Make sure "Sync Address Book contacts" is set to sync "All contacts". For good measure you may want to select "Contacts" under "Replace information on this iPod:" if you don't mind having the Mac overwrite the iPhone on the next sync only.
  12. Click "Sync".

/mac | Apr 21, 2010

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