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Quick problem:

  1. My wife takes videos with her iPhone 5S (with iOS 7.1)
  2. She downloads the videos from her camera roll to iPhoto and removes from the phone
  3. She tries to sync the videos back to the phone through iTunes on her Mac (iTunes 11.1.5, Mac OS 10.9.2) but they won't sync

Yes, "Include videos" is checked and the specific album that has the videos in it has 47 videos on the Mac and shows 47 in iTunes but when they are synced to the phone, we see 27.

This happens with brand new videos taken with the iPhone, synced to iPhoto, deleted, and then synced back - they don't make it to the phone. I perform these exact same steps on my phone (same phone, same version of iOS, same iTunes, iPhoto, Mac OS) and the video syncs to my phone.

I've gone back and forth trying to fix this problem and it seemed like I fixed it after messing around with the sync settings for a long time but we had to restore the phone because her work wiped it when she left and I'm not able to replicate what I did this time..

At this point, I'd really like to just reset the connection between iTunes and the phone and try to sync again like it's a brand new phone. Is there a way to do that?

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I have had similar problems with music and photos. Often, if you look at the files on the iPhone list via iTunes, they will be listed, but grayed out with a 'sync next time' icon next to them.

Somehow, these get in a halfway state, where the iPhone thinks they are queued for sync, but then they never do.

The only way I have found that resolves this issue is to first backup the phone on iTunes, then restore it, which wipes the phone, reinstalls iOS, then reloads your backup. When I do this, the sync list is cleared, and the files will sync as normal.

Good luck!

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