Music app on my Mac can no longer find my music files

You should set the media folder to /iTunesHDD/iTunes/iTunes Media. There will be a hidden preferences file in the active media folder that determines whether Music looks for the artist folder in the media folder (Music default) or <Media Folder>/Music (iTunes default). Change the media folder first then see if you still need to adjust the hiddden .Media Preferences.plist to match the layout of the media. There is an integer value stored in the text file, 0 is without an additional Music subfolder, 1 includes it. Once the bulk of your library is working correctly you can manually move any problem items up or down a layer if needed.

tt2

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

Hello lowellMBA,

Thanks for asking about how to find your music files.

If you know their location, all you just need to go into the Music app, and point it to the new location: Change Files settings in Music on Mac - Apple Support

Then it will play them from there. Thanks.

If everything else is fixed then compare where Music thinks those 17 items should be compared to where they really are, and relocate them by hand. No need to mess with the .plist.

tt2