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unable to sync photos to ipad

Since updating to Mavericks I am unable to sync photos recently added to iPhoto using iTunes. I'm running OSX 10.9.5, iTunes 12.0.1.26 and iPhoto 9.5.1.

I place the photos in an album, but only 103 of the 437 in the album show up in iTunes when I attempt to sync. The 103 photos have been in my iPhoto library for some time. The others are recent. Hope someone can help.

Posted on Nov 3, 2014 2:11 PM

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20 replies

Nov 3, 2014 3:26 PM in response to Amabel

Thanks Leonie. I removed the iPod Photo Cache and tried again, but still no luck


Is enough space on your device for all photos?


Where is your iPhoto Library stored? In your Pictures folder or on an external drive?


Are the recent photos o.k.? Do they show, when you enlarge them? Can you edit them?


Have you repaired the permissions in your iPhoto Library or repaired the library? You can repair the iPhoto Library using the First Aid Tools:

  • Try to launch into the First Aid Tools by holding down the key combination option-command ⌥⌘ and clicking the iPhoto icon to launch iPhoto.
  • Keep the two buttons firmly held down, until you are seeing the First Aid panel.
  • Then select "Repair permissions".
  • Repeat with "Repair database", if the first repair did not help.

Nov 3, 2014 3:55 PM in response to léonie

Still no luck. The iPhoto library is in my Pictures folder, and the recent photos seem fine. I can enlarge and edit them. I tried repairing permission, repairing database and also rebuilding database. Still only the 103 photos are showing in iTunes, and only these 103 will sync to my iPad. I can't see any difference between the 103 photos that will sync, and the other more recent ones - same format and relative size.

I have four iPhoto libraries, and prefer to keep them separate if possible, but I wondered if that could complicate things. I also tried opening a new iPhoto library and importing all 437 photos in this album from a backup file. When I tried syncing the album in my newly created library I still only saw the 103 photos when I went to iTunes.

I can't help thinking I'm missing something very obvious, like some of the settings that I don't always understand completely. But I've never had this problem in the past, and have been using iPhoto for many years.

Many thanks for helping, and I hope there's another suggestion I can follow up!

Nov 3, 2014 5:03 PM in response to Amabel

Can you see the missing photos, that will not sync at all, in other applications? Are they showing in the System preferences, when you try to set a Desktop picture or select a screensaver album? Or in Preview, when you open a photo using the "File > Open" panel and scroll down to the "Media" browser?

This will tell us, if the problem is with your iPhoto Library or with iTunes.

Nov 4, 2014 2:34 AM in response to léonie

I have been experimenting with a few things and think my problem is somehow related to the titles of the photos. When i changed the titles of some of the photos a few of them showed up in iTunes and I was able to sync 109 of the 437, whereas previously only 103 photos showed up. However this didn't work in every case, and some of the photos with changed titles remained hidden so they could not be synced. I can't work out why it worked in some cases and not in others.

Nov 4, 2014 3:17 AM in response to léonie

None of the titles use anything except letters, numerals, an apostrophe, and spaces. They are not very long, maybe four words maximum. The same with the ones that are working and the ones that are not working. Maybe it's the act of changing the title that makes the difference, but it didn't work in every case.


I did read somewhere in my attempt to find an answer that photos without a file extension will sometimes not show up, but adding the file extension made no difference.


I feel completely stumped, and have spend all day trying to find an answer. I've reinstalled iTunes, and experimented with deleting all photos and importing them again. Nothing seems to work, yet I've been syncing this way for many years without any problems. Very frustrating.


Thanks for your suggestions by the way - I learn something useful each time, even though the solution still evades me!

Nov 4, 2014 3:28 AM in response to Amabel

When you tried the Library First Aid Tools, did you also try "Rebuild library"? If not, make a backup copy of the iPhoto Library and then try the rebuild. That will create new preview photos that iPhoto will use for syncing.


Are your photos RAW images or JPEGs?


  • Try to launch into the First Aid Tools by holding down the key combination option-command ⌥⌘ and clicking the iPhoto icon to launch iPhoto.
  • Keep the two buttons firmly held down, until you are seeing the First Aid panel.
  • Then select "Rebuild Library".

Nov 4, 2014 4:04 AM in response to léonie

Rebuild library - actually it was rebuild database in my version - made no difference. And most of the photos are in png format, with a few jpegs. I have been using png because these are scanned images and I create a transparency around the borders in Photoshop so they will print on a coloured background with no white border around the photos. Can't do that with jpegs. Could this be a problem? I've been doing this for some time with no issues, and the ones that appear in itunes are also png format, not only the ones that don't appear.

Nov 4, 2014 4:35 AM in response to léonie

The article says to control click the photo then 'choose Show File from the shortcut menu'. I don't get the option to 'show file'. I can click on 'info' and in each case (photos that sync as well as photos that don't) there is no file extension at the end of the title. However i can't see the actual filename, which I know is different from the title. Where do i find the filename?


If I am to follow the steps in this article it is quite a lengthy process to go through with each individual photo to add the extension so it will sync using iTunes, and I have over 300 I'll have to change. However I'm prepared to do it if it will solve the problem. But I'll try that tomorrow - nearly midnight here, and I'm off to bed. Many thanks for all your help.

Nov 4, 2014 7:39 AM in response to Amabel

I don't get the option to 'show file'. I can click on 'info' and in each case (photos that sync as well as photos that don't) there is no file extension at the end of the title.

In the newest iPhoto use the "File" menu instead:

Select a photo, use the command "File > Reveal in Finder > Original file"

Then check, if the original file has a filename extension.

You may need to change the Finder Preferences in the "Advanced" tab of the Preferences panel to always show the filename extension.

Nov 4, 2014 2:02 PM in response to léonie

Some filename extensions are there, some are not. But this appears to have no relevance to whether the photos show up in iTunes. Some with extensions show up, some don't. None of those without extensions show up, but impossible to say if this is WHY they don't show up. Simply adding the extension to the original file didn't work. The only thing I can point to definitely is that the earlier photos are all there, and the ones added later are not.


And in the 'Advanced' tab in the preferences panel in my version of iPhoto I don't get the option to always show the filename extension.

unable to sync photos to ipad

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