Can't sync ipad, unknown error -39

My ipad won't sync.  I have rebooted my iMac and ipad, trashed the iTunes cache.  I am up to date on software on both machines.  Any suggestions?
iPad is 64Gb, 3G about 40% left on drive

The search bar can be your friend.  Since I'm not familiar with erro 39 on iPad, I typed the following in the search bar:  ipad error 39 and several posts came up.  This one seemed to solve the problem for another person with the same issue:
Looks like you may have a corrupt picture file on the device.
1. Open iTunes
2. Click on your iPad
3. Click on the Photos Tab
4. Uncheck the Pictures (regardless of Automatic sync or manual). You will then be prompted that all your pictures will be removed from your iPad, select Yes/OK.
5. Sync your iPad
6. Check your iPad to make sure that all synchronized pictures are removed.
7. Now, put a check in the Pictures box once again to sync your photos and then run the sync operation once again.

Similar Messages

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    About Disk Utility's Repair Disk Permissions feature - Apple Support
    https://support.apple.com/en-us/HT201560
    Hope that helps ...
    - Judy

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    the ipad cannot be synced. an unknown error occurred -50

    Go here:
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    Everytime I try to sync my Ipod touch I et the following message 'cannot be synced An unknown error occured (13019).  Can anyone help

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  • I get msg iPad cannot be synced. an unknown error occurred. (-50).

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  • How do I fix this? "the iphone can not be synced an unknown error occered. (1140)"

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  • I can't restore my ipad unknown error 27

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  • The iPhone cannot be synced. Unknown error (13019) - anyone run into this?

    The iPhone cannot be synced. Unknown error (13019) - anyone run into this?

    Stephen's got you covered.
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  • I keep getting an error message that says "the ipod cannot not be synced""an unknown error occured (13019).

    I keep getting an error message that says "the ipod cannot not be synced""an unknown error occured (13019). I am trying to put albums on to my ipod by dragging and dropping. I have it set to manually manage music and videos. The albums appear in the music section under Devices, but they don't appear on my actual ipod.
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    I am having the exact same issue as you are with my iPod nano. This started happening the same day after I updated the iPod software, so I wonder if it is a bug within the software that Apple needs to resolve. I dragged 3 playlists of new music from my iTunes over to my iPod and sometime while it was trying to add those songs, the error 13019 popped up. Another note, which may not be related at all, was that iTunes told me at some point during this process (I believe before the error notification, but I'm not sure and that may be helpful to know) that I did not have enough room on the iPod to copy all of the songs, but it would copy as many as it could. What is curious, like in your situation, is now all the songs it supposedly copied appear to be on the iPod under the Device->iPod->Music label in iTunes when it is plugged into my computer, the playlists in question are also showing up there, and it does indeed say my memory is full under the iPod's general tab in iTunes. However, when going through my actual iPod when it is not plugged in, none of those songs or playlists are anywhere to be found.
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  • Ipod cannot be synced.  Unknown error (-48)

    I've had my 80 gig ipod classic for 4 months now, and I've had very few problems with it. Whenever I've had an issue with iTunes not recognizing the ipod when I plugged it in, it was easily resolved with a reset or reinstalling iTunes, or restarting the computer. However, today when I went to add some new files to my ipod, I had to install the newest version, 1.1.1, and after installing that version and trying to sync the files to my ipod, iTunes simply refused. Repeatedly I'd get the error "Ipod cannot be synced. Unknown error (-48). I've been browsing this site and others to find an answer, I've tried all the standard ipod fixes (five Rs) and toggled with the syncing options, namely syncing only checked songs and manual sync, and it won't load any new music either way. I have Windows XP home edition on a Sony Vaio that's a few years old, and I'd really appreciate it if someone could help me fix this issue with my ipod.
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    null

    Oh yes, me too. Two days ago I bought my 160GB iPod Classic, but I have not been able to put anything in it. First the sync seemed to take hours (ca.6GB/1400 songs) and finally I had to disconnect without eject, because the iTunes and my computer got jammed. Again and again the same thing. Unknown error (-48) I recall.
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  • No music after 3.0 upg.: cannot be synced an unknown error occurred (-208)

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  • I keep trying to sync my ipod touch, but it says "the ipod cannot be synced. an unknown error has occurred." what do i do?

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  • My iPod Touch 4G won't let me sync it with my computer, it keeps saying "cannot sync for unknown error" , what should I do?

    My iPod touch 4G won't sync to my computer, it keeps saying "cannot sync for unknown error", what do I do?

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