iTunes: How to Fix the Error for Multiple Missing Music Files (External Hard Drive)

The "missing file" issue with exclamation marks happens if the file is no longer where iTunes or Music expects to find it. Possible causes are that you or some third party tool has moved, renamed or deleted the file, one of its parent folders, the drive it lives on has had a name change, or you've moved a non-portable library to a different path (see Make a split library portable for details). It is also possible that iTunes or Music have changed from expecting the files to be in the pre-iTunes 9 layout to post-iTunes 9 layout, or vice-versa, and so is looking in slightly the wrong place, or that you've been too aggressive when deleting duplicates at some point.

Select a track with an exclamation mark, use Cmd-I to get Song Info, then click No when asked to try to locate the track. Look on the file tab for the location the library thinks the file should be. Now take a look around your hard drives. Hopefully you can locate the track in question. If a section of your library has simply been moved, a folder renamed, or a drive label has changed, it should be possible to reverse the actions. If the difference between the two paths is an additional Music folder in one path then this is a layout issue. I can explain further if that is the case. If everything is where it is supposed to be try Repair security permissions for iTunes for Mac - Apple Community.

In some cases the library may be able to repair itself if you go through the same steps with Get Info, or when playing a track, but this time click Locate and browse to the lost track. It may then offer to attempt to automatically fix other broken links. Although it says something like "use the same location" I think it expects to find the tracks in the same artist & album layout they were in previously, with one systematic change to the path.

If you want me to try to provide specific advice please post back the following details:

1. The location of the media folder under iTunes|Music > Preferences > Advanced
2. The location of a sample missing track shown under Song Info > File > Location that begins file://
3. The true path to the file whose details you gave in 2

See also FixLinks - an AppleScript to repair broken links in Music - Apple Community.

tt2

The filing system on a Mac does a good job of retaining links to files moved around on the same volume, but it cannot automatically repair links when content is moved from one drive to another. Likewise iTunes doesn't automatically repair such links. It will continue to look for media on the old path until the path is updated. Changing the media folder in preferences does not in and of itself do that. The repair mechanism of Get Info > Locate can sometimes work to repair broken links after the fact. I notice your example feature a trailing 1 before the file extension. This is typical of a duplicate file. Perhaps iTunes is less able to repair these. I note too that your external media folder is given as /Volumes/TOSHIBA EXT 4TB/iTunes/iTunes Media. This is good as there is an iTunes folder immediately above iTunes Media. I recommend the following approach

With iTunes closed copy the following from ~/Music/iTunes into /Volumes/TOSHIBA EXT 4TB/iTunes:

• Album Artwork
• iTunes Library.itl
• iTunes Library Extras.itdb
• iTunes Library Genius.itdb
• sentinel {hidden - use shift+cmd+. to reveal}

overwriting any of these files or folders that already exist in the destination.

Press and hold down option as you launch iTunes and keep holding until asked to choose or create a library. Click choose, then browse to and open /Volumes/TOSHIBA EXT 4TB/iTunes/iTunes Library.itl.

This should repair broken links of the type above as you're replicating a type of move that iTunes is designed to cope with, the movement of a library in a portable shape (iTunes folder containing iTunes Media) to a new location. You can try using my FixLinks script to repair any broken links that should remain.

As to why some files have gone completely missing from your media folder I have no explanation. Backups are key here.

tt2

It can help me identify issues if you include the full exact path for 2 and 3, but that's enough for me to understand the background. It would seem that you've manually moved the content from one drive to the other rather than using the iTunes consolidate command to it over and then deleting the originals. One approach is to move everything back where it came from, close iTunes and reopen which should repair the broken links, then consolidate properly. Or you can try using the iTunes repair mechanism I've described above. Or you can try my repair tool.

As for the album you don't have at either path you can see if Spotlight can find one its files anywhere on your system, otherwise you'll have to look to any backups that you have. Is this album on any device?

tt2