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I'm using the Convert higher bit rate songs to 128 kbps AAC option in iTunes when sync'ing music to my iPhone.

iTunes is complaining about three tracks from an album I recently ripped every time I sync my phone. It claims they can't be converted (I rip as Apple Lossless). Unfortunately there's not much in the way of detailed information in the error messages iTunes is giving me.

Does iTunes maintain a parallel, down-sampled, library on disk when I check this option? Could I downsample my Apple Lossless files myself, save them in this parallel library, and stop iTunes from trying to do the conversion on sync? I took a look in my iTunes Media folder for a parallel library but couldn't find anything.

Is the conversion done as the songs are transferred to my iPhone and the converted files live no other place than on my phone?

This is iTunes 10 on OS X 10.6 with an iPhone 3GS.

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3 Answers 3

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I had a similar problem with few of my tracks. The conversion is done live, while syncing. Basicly the problem is with the particular sound track, not the lossless codec (ALAC) itself. I used a third party utility to re-encode the original (keeping it to ALAC) and then iTunes managed to re-encode the track back to 128kBit AAC. Hope this helps.

Does iTunes maintain a parallel, down-sampled, library on disk when I check this option?

No - re-encoding is done live, that's why it's so slow.

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  • Thanks. I did end up trans-coding the files to fix it so this confirms it's the only viable solution.
    – Ian C.
    Commented Mar 18, 2011 at 14:00
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I just had this problem too, and it fixed itself when:

  1. I went to the Music/Songs view and searched for the offending song.
  2. I noticed there were 2 copies of that song listed: one in my library, and one with an iTunes-Store download icon next to it
  3. I clicked on that download icon and deleted the copy in my library.

Upon re-syncing my iPhone, that song copied without issue.

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  • That jives with the need to transcode the file. The one from the iTunes store would have been encoded with the iTunes Match encoder settings so it'd be settings known to work with the copy-as-lower-quality facility of iTunes. Nice!
    – Ian C.
    Commented Jul 27, 2013 at 16:53
  • The odd thing is, both of my copies had been downloaded from iTunes. I'm not sure what happened to the original that it wasn't working.
    – Ed Brannin
    Commented Jul 28, 2013 at 20:28
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I had two songs that did not work. One could be fixed by "remove download" and then pressing the cloud symbol and redownload the song. The other one is still problematic and me be it has to be recoded. I guess apple repaired one of the songs.

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