Why can’t I transfer some songs from iTunes to my iPod?
Question by Cliff /

After restoring my iPod, I get a message on some songs that says: “iTunes could not copy the file ‘name of song’ because the file could not be found.” Some of the downloaded songs from iTunes are not showing up under the directory “iTunes music.” Those songs downloaded or imported from CDs are in my playlist and can be played on my computer, but can’t be transferred to my iPod.

I also had to get another hard drive because of what could have been a virus attack or just a failure, so I restored some of the files from a backup DVD and some were downloaded from Apple’s server with the assistance of a tech support rep. A lot of CDs had to be re-imported. The error shows up on imported and downloaded songs from iTunes. To fix it iTunes support wants $59.00 which I think is a rip-off. Does anyone out there know how to fix these problems?

I’ve seen some answers posted on here about this but the answers aren’t very clear and concise. The details are kind of sketchy or not 100% applicable to my situation. I love my iPod and have hundreds of dollars worth of downloaded songs but this is very frustrating and disappointing to say the least.

Some real help would be greatly appreciated!

tl;dr – I can’t drag some files from my iTunes on my desktop PC to my iPod after doing a restore. The songs are in my playlist and play on the computer fine but some I can’t put back on my device because I get a message that says the file can’t be located. Sure enough, they aren’t showing up in the iTunes music folder. Why weren’t they restored?

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Answers (9)
  • happyboybaby

    We will no longer have to worry “iTunes won’t add music” issue as soon as we get Bigasoft Audio Converter! Bigasoft Audio Converter can convert all kinds of music to iTunes compatible format for fast import to iTunes (including the new iTunes 11).

    It supports converting lossless music formats including FLAC, Monkey’s Audio (.ape), WavPack (.wv), TTA, ATRAC Advanced Lossless, WAV, AIFF, AU, raw header-less PCM, M4A, Windows Media Audio Lossless and Shorten (SHN) to iTunes supported lossless audio format like AIFF or Apple Lossless M4A.
    It also supports converting the above lossless music format to iTunes supported lossy audio format like MP3.
    It can convert lossy music like MP3, Vorbis OGG, WMA, Musepack MPC, AAC, ATRAC and CAF, QCP, AMR, AWR, MP3, RA to iTunes supported lossless or lossy audio format like AIFF or Apple Lossless M4A.
    It even can convert music video in AVI, MP4, MOV, WMV, MKV, VOB, FLV, 3GP and etc to iTunes supported audio format.

    Just google search Step by Step Guide on How to Solve “can’t add music to iTunes” Problem, you will find the ideal audio converter, and a step by step guide

  • Susan Crown

    Easier, open itunes, check the manualy manage music. Sync but don’t check the sync music or anything else. You should be able to retrie the music with a copy-paste.

    If not working, try Sync. It it free for under 1000 song.

  • shane murphy

    I brought a cd off of itunes but it wont go to my ipod.

  • ashley

    Why can I transfer some songs to my ipod from my itunes music library and others wont transfer? I have spent loads of money downloading the music, but they wont go onto my ipod?

  • Jamie VanRaalte

    I’m having similar trouble. Some of them wouldn’t transfer because they were the wrong file type but not all.

  • Kelvin Zhang

    There should be a few options under “File” – “Add File to Library” and “Add Folder to Library”. Use that and synchronise. Otherwise, the songs may be DRM protected.
    -Kelvin

  • franktan

    Whenever you import a song into iTunes, the default is for iTunes to keep a record of your song’s original location, rather than transferring the song file into iTunes. Occasionally you will need to go to > File > Library > Organize Library. This will place a copy of the file inside iTunes folder.

    Also, check your Preferences to make sure that iTunes is copying files to iTunes Media Folder when you add them to your library. You can find this setting at > Preferences > Advanced. Make sure you check that setting.

    • Monica

      THANK YOU IT WORKED! I can’t believe it took me an hour and a half to figure out how to do this. Apple really needs to make this easier for the non-techy people. Thanks again :)

  • ha14

    Some songs in iTunes won’t copy to iPod
    http://support.apple.com/kb/TS1420

    open iTunes select all the music and delete them (do not delete from your hard drive just on iTunes) then From the menu select “File” >”Add folder to library”….select the folder that you keep all of your music files. This erase last played, preference, ratings..

    Preferences – Advanced – General, changed the location of your iTunes Music Folder back to where it should have been

    Rebuild your iTunes library to make sure the XML file is intact and clean
    iTunes: How to re-create your iTunes library and playlists
    http://support.apple.com/kb/HT1451