UPDATE: Workaround for iPhoto 8.1 sync issues with iTunes, iPhone

Edited by Joe Aimonetti

Several users are reporting difficulty syncing their iPhones to iPhoto '09 following the latest iPhoto update, 8.1. Users are experiencing the error code (-50).

Update: It appears as though the bug in iPhoto, which was causing iPhoto Albums to not show up properly in iTunes when attempting to sync photos to your iPhone or iPod touch, is due to corrupt data in iPhoto Slideshows following the iPhoto 8.1 update. Users have found that deleting their iPhoto Slideshows solved the (-50) error in iTunes. This Apple Support Discussions thread reports the many variations of this issue as well as the workaround. Another user suggested simply turning off the music in your slideshows, citing that that would solve the issue as well. MacFixIt reader "Joseph W." reports, "If you disable all music in slideshows, the sync issue goes away." Later in the ASD thread above, Joseph's intel is confirmed.

In summary, first try turning off all the music on your iPhoto Slideshows, then attempt to sync your iPhone/iPod touch. If you still encounter the error, try deleting iPhoto Slideshows. Thanks to our great MacFixIt readers for sending in solutions as they are found!

Updated by Joe Aimonetti, August 25.

ORIGINAL ARTICLE:
MacFixIt reader "Bruce W." writes in to tell us about his syncing issues:

"After upgrading to Iphoto 8.1 I can no longer sync my iPhone. I get a message in Iphoto saying an unknown error (-50) prevented the sync."

Bruce's issue is corroborated by several Apple Support Discussions users. ASD user "viking bear" reports:

"First time I connected my iPhone 3GS to my iMac after upgrading to iPhoto 8.1 I got an error message: "cannot sync iPhone - unknown error -50"

If I decheck "sync photos" in the iPhone sync options in iTunes, it will sync without any problems.

I do not sync all my photos. I have created some albums with the photos I want to sync to my iPhone, and I have checked the box "sync checked albums only". But after upgrading to iPhoto 8.1 it seems like the iPhone cannot recognize any albums at all. The box that used to show all my albums from iPhoto is now empty. I guess thats the reason for the sync error I accounted."

There are several theories as to why this sync error is occurring, though none of those solutions seems to fix the issue entirely. Many believe the error is due in part to corrupt iPhoto Album data, perhaps caused by the update. Users can attempt to rebuild their iPhoto Library:

1. Quit iPhoto and iTunes.
2. Hold (Command Option) and click to open iPhoto.
3. In the "Rebuild Photo Library" window, select the check boxes for:

- Examine and repair iPhoto Library file permissions
- Rebuild the iPhoto Library Database from automatic backup

4. Click "Rebuild".

Other suggestions included resetting or restoring your iPhone, repairing disk permissions using Disk Utility, or running a third party disk check application. I was not able to replicate the issue on my machine, though the issue, as was suggested by ASD user "Terence Devlin" appears to be related to permissions or cache corruption:

"Well I?m on 8.1 and I?ve never synced with my iPhone, so just now I did for the first time and the synce ran with no problems. Then I ejected the phone and re-connected it again and made a few changes, then synced again.

As I?m starting from scratch and you folks have an existing sync, that would suggest a cache issue to me. "

Have you experienced this issue? Did repairing your iPhoto Library help? Did resetting your iPhone? Let us know in the comments!

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