Fixing iPod (Touch) sync on error “cannot enable syncing – Override/Ok”

Today i plugged my iPod Touch into my USB port and got an akward error saying iTunes cannot sync my iPod because syncing is disabled and asked me to enabled it. I clicked yes and got a second dialog saying “Cannot enable syncing” and i could click “Override” or “OK”. The odd thing: both choices yield no success and i was left with a sync of my iPod but without my addresse, calendars, bookmarks being synced 🙁

After some research and luck i found this solution:

First i repaired my file permissions using Disk Utility, even restarted and run the command again -> no luck, but as found here it helped other people.

Then i found out that not only iTunes stopped syncing, iSync itself reports an error message when starting. The message was “Sync Services: Can’t connect to the sync server …” Luckily i found the topic “iSync can’t be launched” at the Apple Discussions.

I deleted ~/Library/Application Support/SyncServices/Local/ and restarted iSync. It took some time to recreate the Local folder, but then iSync started and the syncing in iTunes works again. Just had to enable the syncing for address book, … for my iPod on the “Info” tab.