When iTunes Tunes Out. How to Fix the “was not copied because the file type is not supported” Error Msg

My iMac informed me that I had an update for iTunes. Like I’ve done countless times before, I said, “Sure!” and let the update begin.

I soon realized the error of my ways. When syncing our devices, I was presented with the error:

Some of the items in the iTunes library, including “Born to Be Wild”, were not copied to the iPhone “Edgar Allan iPhone” because they cannot be played on this iPhone.

Followed by a list of over 100 songs, all with a similar error:

“Thunderstruck” was not copied because the file type is not supported by the iPhone “Edgar Allan iPhone”

That’s not all. When selecting the Apps tab, there were songs and podcasts listed. And in the music library, I discovered that the song Long Cool Woman by the Hollies was now an mp3 belonging to Mac Geek Gab. While Dave Hamilton is a fine musician, and his band can without a doubt play a really wicked version of the classic tune, I knew the one in my library was not his band’s rendition.

Even worse, when doing a cursory Get Info on misguided songs and apps, they claimed to be in random folders. Thunderstruck did not belong in Neil Young. Angus Young? Neil Young? I dunno.

Meanwhile, in Apps, Grammar Girl seemed to have been written by Flexibits, who is the creator of Fantastical.

It was as though during the update, iTunes did this:

After trying a bunch of stuff, including reinstalling iTunes, I gave in and contacted Apple. After half an hour, the advisor told me the only thing I could do was to use Time Machine to restore not just iTunes, but the entire machine. Who lead to another advisor, who passed me along to a third advisor. The third advisor had me create a test account and we went down the rabbit hole of re-downloading all the apps and all Apple purchased music. In the end, he thought that perhaps I should reinstall Mavericks from scratch.

To which my reaction was this:

So, while waiting on Apple to call me back–again, I dug in. The test account and subsequent two hours of app downloading got me to thinking. If the same thing was happening to the test account, it couldn’t be something in the user profile. I had nothing to lose since I had backups and I surely didn’t want to reinstall an OS from scratch, which would erase all sorts of tweaks and settings.

After some initial pain, I finally got it all working without reinstalling the OS. I didn’t lose a single playlist or play count.

First, IF your iTunes library is stored on an external drive, and that drive is not a NAS,  try poster David’s suggestion (See the comments section. Thanks, David!). While David’s method did not work for me–it was the same solution a senior tech advisor offered,  it’s absolutely worth a try.

  1. Close iTunes
  2. Open Finder
  3. Navigate to the external drive where you keep your iTunes library.
  4. Count to ten and reopen iTunes.

If it didn’t work, roll up your sleeves and read on.

DISCLAIMER: This is what worked for me. It may not work for you and if you try this, you’re on your own. I’m out of the tech support biz. Oh, and don’t try this without backups, but being so smart, you knew this already.

Part 1: Backups

  1. Make sure you backup your Mac or have a good one already in place.
  2. Go to the local Music folder and rename the folder iTunes to iTunes Old.
  3. Download iTunes again.
  4. Install iTunes, but don’t open it.

Part 2: Restore order

  1. Restore the iTunes folder from backup.
  2. Start iTunes. Yes, yes. I know. You’ve installed iTunes 12, and now you’re using an older version of .itl and subsequent core iTunes files. Shouldn’t work. Right? Keep reading.
  3. Restore all your music files, aka songs, podcasts, etc. NOTE: for me, while the core application files reside locally, my music library exists eternally on my Synology Diskstation.
  4. Start iTunes.

Part 3: Don’t Panic

iTunes will act as though you’ve never run it before. Ignore it.

  1. Locate the Home icon in the upper left (it’s a house with disclosure triangles next to it. Select This Computer (or select your external drive if this doesn’t work for you after the next couple steps). See below.Screen Shot 2014-10-20 at 7.37.46 PM
  2. Screen Shot 2014-10-20 at 7.38.03 PM Select Preferences from within iTunes, then Advanced.
  3. Point iTunes to the location where you keep your actual music files.
  4. Quit iTunes.
  5. Restart iTunes.

Rock on!

Did you find this article helpful? No purchase necessary, but please do me a solid and check out my books. If you like what you read, for the cost of a cup of coffee you will have found a book to read and hopefully solved your iTunes issue.

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22 thoughts on “When iTunes Tunes Out. How to Fix the “was not copied because the file type is not supported” Error Msg

  1. Thank You Thank You Thank You.

    This worked brilliantly for me, though I went about it a bit differently than you did.

    1) rename iTunes library (in Music folder) to “iTunes – OLD”
    2) deleted iTunes (must right-click, ‘Get Info’ and set permissions to read/write for all users (Group, Wheel, You, etc.)
    2a) looked for iTunes in the App Store Updates, but it wasn’t there.
    2b) restarted and looked again, still wasn’t there.
    2c) panicked a bit
    3) opened Time Machine and navigated to the last time I knew iTunes worked (two days ago) and restored iTunes and the iTunes Music folder from that day
    4) re-downloaded all the podcasts and app updates from the past couple of days
    5) Sync the iPhone and…
    Success!

    Thanks again!

    • Had a similar problem again, found this post again, and tried something different before nuking iTunes.

      1) I renamed the iTunes folder to ‘iTunes-old’
      2) I opened iTunes and it pretended like we had never met before. I waited a bit till it recognized my iPhone and found my purchase history.
      3) I closed iTunes
      4) I renamed the new iTunes folder to ‘iTunes-new’
      5) I renamed the old iTunes folder to ‘iTunes’
      6) I started iTunes and went to sync the phone again and it worked with no issues.

      Quirky, indeed.

  2. I received the error message for 100 songs – but checked my iPod… And the songs iTunes told me could not be copied were still there! Relief! Any explanation? Should I expect them to disappear?

    • I got the same thing. I found out that iTunes was including copies of songs that my Synology copied, then changed the name of before trashing them. Like you, the songs were all on my iPod and play just fine. Once I emptied the Synology’s recycle bin, all was well.

  3. I have found what might be a MUCH quicker solution –

    I get this error message with iTunes when syncing my iPhone/iPad. My music is on another drive and I think it’s as simple as it can’t be found by iTunes. There is no message to say it can’t be found, only this error message when trying to sync an iPhone/iPad.

    The solution that works for me is this:-

    1) Close iTunes
    2) Go into Finder and navigate to the external drive with your music/movies/apps. This lets your computer spin that drive back into action, knowing it’s about to be accessed.
    3) Count to ten and reopen iTunes.

    iTunes then seems to find the files it doesn’t even know its missing. Syncing then works fine for me.

  4. I am a very non-technical person when it comes to things like re-installing etc. I found this page because I had pretty much the same issue – I had a new iphone, and at some point the iTunes on my desktop corrupted and lost most of the playlists. I waited nearly a year before trying to patch together playlists onto my brand new macbook… and of course that means synching my phone to a new iTunes. Once I felt I redid my playlists well enough (because of course syncing my phone erases everything I rightfully already own on the phone and won’t let me pull playlists from it)…

    It synced and came back with that error message, tons of my music THAT HAD JUST BEEN ON MY PHONE was now somehow not the right format.

    I solved it in the least technical way possible.

    1. I got the pop up of 100 (yeah, right, 100… I’m sure that’s lazy programming limiting it to 100 errors). I decided after the pain of redoing playlists… I made the pop up window as long as I could and used my camera phone to photograph all the songs that weren’t transferred.

    2. I kept my phone plugged in, opened to see what was on the device, and had my full song library open. I found each song (at least they’re in the order that they’re in the library) and mouse click grabbed it and dropped it onto my iphone device in the left hand column.

    3. As I did this, the songs actually filled in to the playlist they were supposed to occupy. While doing this, it started showing pop ups individually for songs that weren’t syncing so I just click grabbed each as it popped up and dropped it on top of the ‘device’ iphone icon on the left column. And I just kept whack-a-mole adding them as they popped up.

    4. I think synced my phone again – did I say I’m non-technical? It of course went through all 1571 songs AGAIN (they were all greyed out on my phone as it began) and after this last sync….

    All songs are on my iphone, so far as I can tell. No re-install and no guarantee I don’t have this problem again, but at least it’s an option (probably no more time consuming as the install/re-install path) for the less technical.

  5. David, you were spot on in my case. After moving my iTunes install to an external drive, I got this issue. But after spinning up the drive, the second attempt worked fine. Thanks for saving me and hopefully others a LOT of time by avoiding trying the other suggestions.

  6. All this can be reduced to the following:

    First disconnect your iPhone/Pod/Pad, then

    1 Go to advanced settings in iTunes Preferences

    2. Select the location of your iTunes Media folder

    3. Restart iTunes.

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