Apple Music playlist loses links to songs

The default location for a Music library in Catalina and later is ~/Music/Music with the media files consolidated into ~/Music/Music/Media. After importing your iTunes library you may want to copy your active Music Library.musiclibrary file into ~/Music/Music replacing any older copy there, then use Music > Preferences > Files to reset the media folder path, and File > Library > Organize Library > Consolidate Files to bring all the music into media folder. You can then remove the originals from the old iTunes Media folder.

Follow the guidance in these articles:

Managing your Mac media libraries - Apple Community

Use the Finder to sync your iPhone, iPad, or iPod with your computer - Apple Support

Move your iTunes library to a new computer - Apple Community

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.

See also Managing your Mac media libraries - Apple Community. iTunes Music is the old name for what become the iTunes Media folder, which in turn would normally be called Media in Catalina or later. It may help to bring your media folder structure up to date.

tt2

So in this example Music was looking for the file at:

My Passport for Mac/iTunes/iTunes Music/Joe Pass/The Best Of Joe Pass/Aaron's Song.mp3

(I'm assuming /iTunes Music/iTunes Music/ was a typo) when the true path is:

My Passport for Mac/iTunes/iTunes Music/Music/Joe Pass/The Best Of Joe Pass/Aaron's Song.mp3

where the difference is an extra /Music folder in one of the paths.

See Managing your Mac media libraries - Apple Community and the section on iTunes Media Organization for background info. It seems you may have a mixed layout with some files in the new layout and some in the old, but the database looking for everything in the old layout. Changing the layout flag from 0 to 1 may repair the links to tracks that are currently broken and fall into the same general pattern, hopefully without breaking anything else. The alternative approach is to move the files from the current location to the expected path, but you need to be careful not to overwrite any folders taking this approach (i.e. moving an artist folder from iTunes Music/Music to iTunes Music) as Mac doesn't merge folders and this could lead to data loss.

tt2

For the avoidance of doubt this is a user to user support forum. I don't work for Apple Support. I do have have a reasonably deep understanding of the way Music and iTunes handle files. The fact that you're repeatedly relinking files by hand suggests the work you're doing isn't being saved, which is a worry. Do you have any third party security software? If you locate the Music Library.musiclibrary package you can right-click on it and click Show Package Contents, do you see any hidden .tmp files inside? These would indicate interference with the way that Music updates the library.

tt2

So if Get Info shows:

file:///Volumes/My Passport for Mac/iTunes/iTunes Music/iTunes Music/Joe Pass/The Best Of Joe Pass/Aaron's Song.mp3

what is the true path to the file:

Aaron's Song.mp3

If you search for it using Finder?

tt2

Given that you are running macOS 13.2 Ventura you should be using the Music app, not iTunes, and you should be opening a Music Library.musiclibrary database. While Music can open .itl files and convert them to the .musiclibrary format, and changes are made to the .musiclibrary file, not the .itl.

From your example entry file:///Volumes/Main File Drive/Users/rldbtr/Music/iTunes/iTunes Music/Ademilde Fonseca _ Galo Garnizé/Cafe Brasil/Ademilde Fonseca _ Galo Garnizé.mp3 what would be useful to know is the true location of the file Ademilde Fonseca _ Galo Garnizé.mp3, assuming it exists somewhere on the My Passport for Mac drive.

As above see Managing your Mac media libraries - Apple Community for some background on how things are ideally organized. The script I mentioned earlier can be used to repair tracks when they are in the standard layout of <Media Folder>/[Music/]/<Album Artist>/<Album>/[D-]## <Name>.<Ext>. From the look of your example the files may not be in this layout. If the path can be reliably predicted from the file properties the script could be tweaked appropriately.

tt2