upgrade from high Sierra to Catalina

Do you have a pre-upgrade backup of your system in Time Machine or similar? Rolling back might be an option if you do, otherwise not. You can try option-starting Music and then selecting your old iTunes Library.itl file to see if it does a better job of converting your old library.

tt2

Rats. Not so good.

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://localhost/
3. The true path to the file whose details you gave in 2

tt2

I was referring to this....

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://localhost/
3. The true path to the file whose details you gave in 2

tt2

I need the precise information for these details if I'm to get a clear picture of the state of things and be able to suggest a resolution. I've copied one of my tracks to a new path and then deleted the original to recreate this type of issue on my computer. Here are my three details.

• 1. Location of media folder in preferences:

/Data Drive/steve/Music/iTunes/iTunes Media

This is the actual value from the dialog box. I'm using a library on an external drive that was previously being used with Mojave so is still in the original iTunes Media folder. Music may or may not be using the correct path after you imported your .itl file.

• 2. Here is the dialog box i get if I use Song Info (Cmd+I) > File tab on the track that I've broken. The value is:

file://Volumes/Data Drive/steve/Music/iTunes/iTunes Media/Music/Aaliayah/Aaliyah/15 Messed Up.mp3

(file://localhost must be Windows specific)

• 3. Here is the actual location of the copied track that Music cannot find automatically because it is neither in the last known location, nor the expected location for the current library options:

Volumes/Data Drive/steve/Music/iTunes/iTunes Media/Aaliayah/Aaliyah/15 Messed Up.mp3

In my example case I've removed one of the Music folders from the path, and I could repair the broken link by moving the folder Aaliyah from ../iTunes Media down into ../iTunes Media/Music. I'm hoping that with similar information about your library I might be able to suggest a simple move that would repair things, but I need the precise details to work with.

tt2

Glad it worked out. 🙂

tt2

If you supply the three items of information I may be able to speed things up for you.

tt2

Your 2 and 3 aren't talking about the same track. Are the music files in Users/Philip/Desktop/iTunes/iTunes Media or Users/Philip/Music/Music/Media?

tt2