iTunes 7 sync problems and large libraries on external drives

Update: This problem seems to have been addressed in a recent update to iTunes. The program now stops looking around 100 missing files before giving the warning dialogue. So if you’re having this problem, make sure you’re using the latest version.


One of iTunes 7 handy new features is the “sync problems” warning. The screen pops up whenever you try to sync your iPod with your iTunes library and song/video/podcast files cannot be found. Previous versions of iTunes only let you know there was a problem; iTunes 7, however, helpfully tells you which particular files are missing.

It’s a nifty function for tracking down errant files that iTunes has somehow lost or forgotten about. or which you may have accidently deleted. But that helpfulness can cause problems in certain instances.

You see, I have a rather large iTunes library: 14,000+ songs that take up ~78GB of hard disk space. So I keep all my song files on a dedicated external hard drive, a hard drive that isn’t always turned on.

In previous versions of iTunes, if song files could not be found when attempting to sync your iPod, you would just get a warning about a single missing file, but all your recent play stats (play count, star ratings, last played) would still be updated from the iPod into the main iTunes library.

However, when doing the same thing in iTunes 7, the program begins to compile its detailed report. In my case, if the external library is not mounted on the desktop and i try to sync my iPod, iTunes then starts trying to find all 14,000+ missing song files.

The program seemingly freezes (the dreaded beachball) while it is processing all those missing files. The only options are to wait for it to finish (which takes more than an hour on my Intel iMac) or force quit (and lose any stored play count and last played data from the iPod). I found this out the hard way, twice, before I realized what was going on.

So, just a quick word of advice: if you’ve got an external library, make sure it is powered on and mounted before opening iTunes.

31 thoughts on “iTunes 7 sync problems and large libraries on external drives

  1. I have itunes 7 and my library was full and songs wouldnt fit on my ipdo
    so it made a select list of songs that would be synced onto my ipod.
    Then i deleted songs in my library so that all of the library could fit onto the ipod
    Then i deleted the selected list of songs.
    Now none of my songs will sync with my ipod and my ipod currently has no songs on it
    Is there anything i can do??

    tunequest Reply:

    From the sound of it, Nora, you might be out of luck. If I’m understanding you correctly, it sounds you deleted the music from your library that your iPod needs to copy from.

    If you just removed the entries in your library and not the music files themselves from your hard drive, then you can easily re-add them to your iTunes. Otherwise, you’ll have to re-import/download/acquire them.

    I wish I could be of more help, but really this isn’t a support site. It would take more time than I currently have to properly diagnose what’s going on.

    However, I can point you in some good directions. Apple’s support discussions are full of knowledgable people who enjoy answering questions:
    iTunes for Windows:
    iTunes for Mac:

    Also try the forums at MacRumors. They’re usually bustling with activity.

    Good luck!

  2. I am just recovering from the same problem. I completely reset my iPod (4th G), connected it to my laptop (Windows XP SP2), and, in iTunes, changed from automatic synchronization to manual, opened the “Music” tab at the top, checked off Music and various playlists I wanted to synchronize, clicked “Apply” (lower right corner) and, voila, iTunes started synchronizing again. Hope it works for you as well.

  3. So how do you remove the offending errors? I deleted those files (within Itunes) a while ago, yet now I have 70 errors–all due to podcasts, but can’t figure out how to remove the references, and hence errors, to these files?

    tunequest Reply:

    From any of the source views, you should be able to select any song or podcast with an exclamation point next to it and press delete. From any playlist, press option-delete on a mac and alt-delete on windows.

    For batches, try the Super Remove Dead Tracks Applescript (mac only). On Windows, you’ll need the RemoveDeadTracks.js file, which is a part of the iTunes SDK for Windows.

    yachtman Reply:

    The ‘Super Remove Dead Tracks’ did it. However, it says that it removes (!) files, yet, none of these files could be seen in iTunes 7.1. They were all podcasts that I had deleted and unsubscribed to. Anyway, it worked–Thanks!

  4. I tried to synchronize two songs to my iPod right now but when they got in neither in my iPod nor the playlist that shows of my iPod in itunes plays it but when selected in the music playlis that’s default in iTunes my music does play.what can I do?

  5. I have a 80GB ipod, and Itunes 7 with windows XP. I can not sincronize it. Apparently it works on my computer screen, the ipod on the itunes its sincronized, but then, when I disconnect the ipod and check the songs, there is nothing in it.
    What can I do?

    tunequest Reply:

    Try reformatting it. Here’s instructions from Apple.

    John Reply:

    Be careful following the instructions from Apple on large hard drives. Windows XP can’t seem to format large FAT32 partitions. Somewhere on a Google search I came across an HP USB FAT32 drive format utility. This did the trick for me!

  6. Well i went over to my friends house and when I thought it was about to sync and add his music on my ipod it erased all my song and replaced them with all of his! I tried to put the songs back to my ipod by connecting it to itunes and expecting it to sync all of them back. But it didn’t. Now when i click music (next to where my ipod is in itunes 7) it says i have to delete all the songs to have them replaced.

    Is there some option I can do to fix it from not deleting.

  7. I’ve just got a new ipod nano but when I try sync it it always says iPod ‘Jamie’s iPod’ can’t be synced. The required disc could not be found. The problem is I did’nt get a cd with my ipod. Nor did I get one with my last iPod nano. What do I do to make it work? Help would be appreciated.

    miles Reply:

    my ipod video does the exact same. “the required disc could not be found” if you find out how to fix it can u please email me back coz its starting to piss me off

    Jimmy Reply:

    exactly the same problem with my second gen ipod shuffle. ive got the latest itunes and XP SP2

    Sajan Mathew Reply:

    the same happens to my ipod also (ipod nano video), I synced it to other PC, it synced proprly, if I synced my ipod with my pc, the message comes ‘the required disc cannot found’

    dESi Reply:

    did u figure out how to fix it bc my ipod shuffle is doing the same thing and its makin me mad. i even tried to uninstall itunes and reinstall it and same thing happens.

  8. Ive got the Same Problem with my ipod shuffle. My Friend gave me the ipod but she didnt give me a disk with it. Its driving me crazy!!!!! Help me…

  9. is it really true that i can only sync my iPod to 1 library only? cause i want to add songs from my other pc and its giving me this message

    The ipod (name of the user) is synced w/ another itunes library. Do you want to erase this iPod and sync w/ this itunes library?

    tunequest Reply:

    Yep, it’s true, if you use iTunes to automatically manage your iPod. It can only be synced to one library at a time.

    I’ve never tried it, so i can’t say for sure, but if you switch to manual ipod management, you might be able to drag songs from multiple libraries.

  10. I have an Ipod Classic 80Gig and when I sync it up, only a few of the tunes get loaded up, not all of them, same with video. It’s hooked up to a USB2.0 through a Windows Vista HP computer, is Vista the problem? or something else? Everything is updated, Itunes and Ipod. Please help, I’m very frustrated!

    tunequest Reply:

    Honestly, I can’t help you. I don’t know anything about Vista or the newest iPods. All I can really do is direct you to the help forums listed at the top of this discussion. You might be able to find some solutions there.

    Good luck.

  11. I started having syncing problems after I downloaded iTunes 7, now, hard as I try, 5 R’s and other manual fixes, ipod does not sync AT ALL. I’m very frustrated for I have both 30 GB and nano ipods. I can’t do anything with them because it just won’t sync them. What to do, what to do……anyone please help.



  13. when I try to synch from Itunes to Ipod either music or podcast after a while get a warning The POD named cannot be synced- unknown error occured (-39) I do not know if this is a fault of the IPOd or of Itunes any help please.

  14. i have a similar setup. windows machine, itunes 7.6, external drive with all my music on it. iTunes knows about the music being on external drive. i have an ipod Classic 80GB.

    here’s my problem. every time i sync my iPod Classic it deletes 2000-3000 tracks and resyncs them from the external drive as if they had changed. it’s insane. not only does it take forever to sync up (frustrating) it thrashes my external drive and the ipod’s drive needlessly which certainly is going to hurt their lifespan. note at the end of the sync i have the same amount of songs on the ipod. it just deletes and resyncs stuff over and over.

    driving me nuts. any ideas?

    tunequest Reply:

    Hi popmonkey

    I’ve seen this happen before with my older model iPods and I’ve never been able to figure out why. My hunch is that it has something to do with my Smart Playlists—that somewhere in the update cycle, some songs get removed and re-added to the playlists, prompting iTunes to remove and re-copy them.

    Other than that, the only suggestion I have would be to wipe the iPod and copy your songs over again.

    popmonkey Reply:

    thanks tq,

    i’ve wiped the ipod 4 times now with no effect. i’m starting to think that maybe itunes is acting silly because the files have album artwork embedded in them.

    i got an interesting suggestion on the apple forum. a guy suggested i mark all the music files read-only.

    i also will monitor write activity (attempts) form various software to see if maybe something outside of itunes is causing files to get updated enough that itunes wants to resync.

    it’s definitely not a playlist issue because i copy all my music to the ipod.

    thanks for your comments, i’ll report back how the read-only thing works out.


    popmonkey Reply:

    my problems went away when i got rid of album art that was embedded in the id tag. i know, i don’t understand it either. i used mp3tagger to remove the images, re-added the images using itunes and now it’s fine…

    /me shrugs

  15. I have a 160gb ipod classic…I have tried to sync it first to an external drive and it freezes towards the end. I then created the itunes library on my laptop and it is doing the same thing…please help. I have itunes 7.6 and version 1.1.1 of the ipod software

  16. Itunes is shit, plain and simple…….. My library keeps getting deleted, my itunes won’t recognize my ipod anymore… I paid all this money for what? Nothing… Bull…Shit.

  17. I have the same problem as some people above..

    I plug in my ipod and it says the disk could no be found, nor written to.

    In addition to this, it sometimes says that “the required disk could not be found”

    The stupid thing is, is that the music files are on the computer!!

    This all started by me plugging in my ipod to charge it, thats all!

    Any help would be eternally apreciated…
    Please e-mail me to help me fix it, PLEASE!

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