How to fix this issue and sync iTunes to iPhone correctly?

OS X Yosemite, iPhoto 9.6.1, iTunes; iPhone 5, iOS 9.3.3

I imported my pictures to iPhoto then tried to sync some unrelated changes to the iPhone through iTunes and got this error message. Restarting iPhoto and iTunes didn't help this time.

Disclaimer: I found the solution to this specific issue and I'm using this space to share it with others. Other solutions may be valid on different situations. I remember fixing this once by restarting the Mac.

Here are some links related to this problem with some "heavy weight" solutions I didn't try this time:

  1. http://osxdaily.com/2013/06/30/itunes-not-syncing-iphone-ipad-ipod-fix/
  2. https://discussions.apple.com/thread/6831863
  3. https://discussions.apple.com/thread/7180697

After restarting both iPhoto and iTunes a few times and trying it again, eventually I decided to (1) delete the previously imported photos on iPhoto: enter image description here

Since I didn't want to delete them, (2) I created a new album with them and, once back to iTunes, (3) checked the new album to be sync'ed back to the iPhone.

It worked!

  • It seems like the integration of these systems expects you to take some action after importing pictures (like deleting them) and manage them through iTunes... – Ricardo Aug 4 '16 at 18:31

I've just had the same problem. This helped me:

  • On Mac, terminated the Photos app
  • On Mac, terminated the iTunes app
  • On iPhone, performed force restart

After that, syncing worked again.

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