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I got this error trying to sync from my Macbook Pro (OSX Yosemite, 10.10.5) to my iPhone SE:

iTunes could not copy "The Song Remains the Same" to the iPhone "Dan's Phone" because an unknown error occurred (-5000).

Oddly, the problem didn't occur with my previous iPhone 5s. How do I fix it?

  • I have the exact same issue - except that my ITunes is on a Windows Laptop. Can you please help me in terms of what changes I need to do. Thanks in advance. – Rajesh Apr 23 '18 at 10:50
  • On windows, I imagine the basic process would be similar. Note the song that fails, assess it's permissions and other attributes, and then correct it's permissions. I haven't used windows in ~10 years though, so can't offer specific help. You may do better opening a new question, and you'll need to provide more information for anyone to help you (i.e. windows version, etc). – Dan McCarthy Apr 26 '18 at 14:33
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The solution was simple - it was a permissions problem. On the Mac, here are the steps I took to fix:

  • Note the song that fails, on my case it was a Zeppelin song.
  • Using the terminal, cd to the directory containing the song
  • Run ls -la and note the owner/permissions of the file that fails, in my case it was an alternate username I was using at one point, let's say that username is paulhewson, and your real username is hewson
  • Run sudo find . -user paulhewson from the top level music directory (~/Music), this shows all the music that is owned by this alternate user
  • This command will change the owner to your normal username: sudo find . -user paulhewson -exec chown hewson {} +

I suspect this error could result from any sort of permission problem, in some cases maybe read-only or locked files, in which case you'd want to chmod or unlock the files. If there are multiple types of permission problems, you may need to repeat this process a few times. Might be easier to chmod/chown everything in music, but I tried to avoid that so I didn't cause other issues.

Credit to this question for help with the find command to change ownership: Change owner for all files owned by x

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