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iTunes won't sync with photos included

I've read a lot about this on the web, but can't seem to find anything consistent and the "solutions" I've tried haven't worked anyway. So here is my situation and maybe someone can offer something I haven't tried:


I bought the a new iMac 21.5 when they last were upgraded. I took a backup of my macbook and loaded that into the new iMac.


I hadn't paid much attention to the syncing of photos because I don't do many, but last night I was trying to get some new pics and videos I had gotten into iphoto on the iMac to sync to the iphone. I was surprised when they didn't show up on the phone and then I saw that the checkbox to sync photos was not checked. When I marked it, it wouldn't sync at all (got error -50). Same thing happened with my new ipad mini as well as on old iphone 4.


I took my iphone to school, where I had moved my laptop, and tried syncing there. I was surprised that the photo checkmark was not marked on that one either so I have no idea when that change happened. Anyway, after marking it, the phone was able to synce with the laptop after I approved it as "trusted".


Back on my iMac, I still can't sync though, if photos/videos are included.


Any ideas on what I can do?

Posted on Apr 16, 2014 11:53 PM

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Posted on Apr 18, 2014 7:25 PM

I may have finally solved it. Talked to Applecare for awhile though what they thought was the problem doesn't seem to be it. They seemed to feel it was a corrupted picture on the iphone that wasn't getting deleted properly. I thought about that, but if was a bad photo (or video) on the phone, then it shouldn't have synced with the macbook either. So I decided it was more likely that any bad picture had been transferred to iphoto, but then it wouldn't sync back. Recent photos and videos were never uploaded to the macbook, so it would still work.


Anyway, following their advice, I restored from a backup (they felt this would clear the bad photo from the phone. As I expected, it still didn't work. But I had an empty iphoto library too so I switched iphoto to use that one. Sync worked. Of course, no photos so I still have to go back to the other library. I have, so far, copied all the files "imported in the last 12 months" to a folder on my computer. Then I sorted all the photos in iphoto by date and deleted those that didn't matter to me.


And then started the sync, which is working so far though a long way to go. Still, I'm well past the point where the error showed up. If that works, I'll look at the photos I put in the computer folder to see if I want to keep any of those and little by little import them into iphoto and keep syncing. Hopefully whatever file was causing the problem isn't one I need to copy back.


When I get through all this stuff, I'll post what I hope will be a final update.

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Question marked as Best reply

Apr 18, 2014 7:25 PM in response to dbk9999

I may have finally solved it. Talked to Applecare for awhile though what they thought was the problem doesn't seem to be it. They seemed to feel it was a corrupted picture on the iphone that wasn't getting deleted properly. I thought about that, but if was a bad photo (or video) on the phone, then it shouldn't have synced with the macbook either. So I decided it was more likely that any bad picture had been transferred to iphoto, but then it wouldn't sync back. Recent photos and videos were never uploaded to the macbook, so it would still work.


Anyway, following their advice, I restored from a backup (they felt this would clear the bad photo from the phone. As I expected, it still didn't work. But I had an empty iphoto library too so I switched iphoto to use that one. Sync worked. Of course, no photos so I still have to go back to the other library. I have, so far, copied all the files "imported in the last 12 months" to a folder on my computer. Then I sorted all the photos in iphoto by date and deleted those that didn't matter to me.


And then started the sync, which is working so far though a long way to go. Still, I'm well past the point where the error showed up. If that works, I'll look at the photos I put in the computer folder to see if I want to keep any of those and little by little import them into iphoto and keep syncing. Hopefully whatever file was causing the problem isn't one I need to copy back.


When I get through all this stuff, I'll post what I hope will be a final update.

Apr 19, 2014 10:47 AM in response to dbk9999

Well, I'm not sure about some of this, but I was able to sync with photos/videos included on my iphone 5, ipad mini, and old iphone 4. However, I don't get the same thing on all of them for some reason. I think the iphone 5 and ipad mini are pretty much the same though I haven't compared all those pictures of course, but the iphone 4 wasn't. Not a huge concern since I keep it just as a backup phone in case my other one gets lost.

iTunes won't sync with photos included

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