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I have a 160GB iPod and it only syncs old music to my iPod.

I buy new songs and it will not sync them. I have probably 150 songs that will not sync (purchased songs). I did run diagnostic and it says iTunes helper is not working. Not sure what that is and not sure if it has anything to do with it.

How can I fix so that all songs sync to my iPod?

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Did you try rebooting your computer and restarting iTunes? Are you running OS X or Windows? Where did you purchase the songs from, in which format (MP3, AAC, WAV) are they? – patrix Dec 21 '12 at 6:03

Make sure that in iTunes that you have it set to sync your "Entire Music Library":

  1. Open iTunes*
  2. Connect your iPod
  3. Select it in the iTunes sidebar
  4. Click the "Music" tab
  5. Ensure "Sync Music" is checked
  6. Select "Entire Music Library"

*This assumes you are running a fairly recent version of iTunes.

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