iPhoto library won't sync to iPhone 4

Was having the same weird problem. I was trying to sync 4 folders with between 500 and 900 photos each (totaling 450MB). The first 3 attempts nothing happened. Then iTunes created a photo cache folder for the first two folders, then started over and created the cache files for the second two, but still wouldn't sync them. I had about 2GB free. I removed another another 2GB of music and this time all 4 folders synced, but in reverse chronological order rather than by file name. Will call Apple support and see what they say.

Great. Thanks for sharing your solution. I was having the same problem, tried your suggestion, and now everything works as it should.

Thanks for posting!

The power-cycle "fix" doesn't work for me either. Does Apple look at these boards or are we just supposed to blunder upon a "fix" by ourselves??

It's unfortunate that Apple's updates these days seem to introduce more new bugs than they seem to fix (which is the reason I try to update as little as possible, but stupidly I updated iTunes a while back and this photo sync bug surfaced). I've tried the new iTunes 9.2.1 update but it does absolutely nothing to fix what must be a phenomenally simple thing to fix. Getting reaaally bored now...this really is page-one/line-one of what a smartphone should be able to do but I guess Apple have got bigger fish to fry with their iPhone 4 antenna debacle 😟

To summarize, from this thread it seems this bug is common to the following:

iPhone 3G (in my case)
iPhone 3GS
iPhone 4

iTunes 9.2
iTunes 9.2.1

iOS 3.1.3
iOS 4

Mac OSX 10.4.11
Mac OSX 10.6.4

Helloooo...Apple...anybody out there??!!!

I found that I can't include videos from iPhoto or it will not sync all the photos even though there is plenty of room for both. After getting the photos on the phone, I tried reselecting to include videos and it actually deleted most of the photos before giving me the 'out of memory' error again. I've tried deleting all the appropriate folders on my Mac and iPhone and syncing again, but it will not work as long as I include videos.

I have an iPhone 3G that I upgraded to IOS 4.0.1 and my photo library stopped syncing too. I tried all the methods mentioned here and none of them worked. I decided to make a backup copy of my library onto another drive to try syncing to it instead and was checking to make sure I got all of the folders copied when I noticed one folder titled "iPod Photo Cache". I deleted that folder from my original library, went back to try syncing to it one more time and voila... My photos optimized and loaded onto my phone again.

The "delete iPod photo cache" fix definitely doesn't work for me (although I'm on iOS 3.1.3 on an iPhone 3G with iTunes 9.2.1, Mac OSX 10.4.11 and iPhoto 5.0.4 (I wonder if this old version of iPhoto might actually be the culprit??)

This is not the first time for me. iTunes will no longer sync iPhoto to either my iPod Touch or iPhone 3Gs. The only way I can get photos into either device is to create a folder on the desktop and copy photo folders to that. iTunes then "sees" them and syncs normally. If I select iPhoto as the source, it stops half way through with the message that a file "can't be found". No mention of what file, which is very helpful.

I had the same problem. In iTunes, I clicked on my iPhone and then the 'Photos' tab and clicked the 'Synch Photos From' box and all was well

Honestly, I've had this same problem ever since switching to iOS4 and my new iPhone 4 and I'm not sure why. I live in Philadelphia near two Apple stores and went to FOUR Genius Bar appointments for help with the issue. All the employees were as helpful as they could be and even swapped out my iPhone 4 thinking that would fix it initially, then did an "Archive and Install" on my MBP... nothing as worked and every time I sync photos back to my iPhone via iTunes I need to shut down the phone and turn it back on. I really wish Apple would address this issue.

I'm having the same problem: 1) not all pics sync from iPhoto 2) none of the videos from iPhoto sync (I do have the "include videos" box checked in iTunes

Calling Apple Tech support right now.

Hi there, I had this problem so I deleted my photo cache and it optimised all my photos again (9000 of them :)) but it worked!!

I've been annoyed by this for a while, but I got this to work correctly. I searched for "iPod Photo Cache", deleted that folder then re-synced the iPhone. It worked fine.

Hello, I found a work around en exported all the photos destined for my i-Phone from Aperture to dedicated folders and clicked these folders for synchronization in i-Tunes.
Worked perfect and at least I have my photos on my i-Phone until Apple fixes this issue.

Hello, I have some issues whit sync. When I mark in itunes to sync my photos, there is an error msg...the required files cannot be found. ***? Help pls 🙂