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.
2.  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.

Amazon    B&N    iTunes    Kobo    Books A Million    Audible