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File could not be found Error

Just thought I'd mention something I've run into recently with my old Shuffle.

I have things set up to be manually managed because Syncing is a mess dealing with all my iDevices so I've grown accustomed to dragging over music manually to my 2nd Gen Shuffle but I've run into this error when doing so:

"iTunes could not copy "song name" to the iPod "iPod name" because the file could not be found."

Which is bizarre because the song is already in iTunes. The way to fix it is to turn OFF "Convert higher bit rate songs to 128 kbps AAC".

It only happens on some songs and I can't find a commonality between them at all. Also I've noticed that when iTunes throughs up this error the Shuffle mounts on the desktop briefly then unmounts. I have it set to not use it as a disk in iTunes.

Has anyone else seen or dealt with this error?

Too many to list, Mac OS X (10.6.4)

Posted on Sep 8, 2010 10:44 AM

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5 replies

Nov 13, 2010 8:08 PM in response to W. Raider

Fantastic, thanks so much for figuring this out.

I was having the same problem, with the same three files failing every time I tried to sync my iPhone. But iTunes could locate them fine via Show in Finder. Even tried making copies of the files, deleting them old ones (from both my Library and the machine), and then importing the copied files back into iTunes. And the same "file could not be found" message still came up, every sync, now on the cloned files.

Turning off the AAC conversion made it go away. Completed sync on the first try, no errors.

Thanks again!

File could not be found Error

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