iTunes libraries on external 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

Press and hold down option as you launch Music, choose the iTunes library, save the converted Music library in a suitable location. Close Music and move the new Music Library.music library into the same folder as the old .itl file. Open the .musiclibrary file in future.

tt2

I prefer to keep iTunes on an external drive. My 2011 iMac died. I now have a new iMac (fun).

I have itunes on my external drive but am having trouble mapping it Apple Music.

I've got to the Choose Music Library prompt, selected Choose Library, selected iTunes, selected iTunes Media (is that correct?), selected Music then I'm take to a listing of all of my different artist.

Do I have to select each song, what about my movies and books?

Do you have an iTunes Library.itl file on the external drive? If so this would be your old iTunes Library which Music can convert to the new Music Library.musiclibrary format. Assuming this works you can save the converted library in <External>/Music. If you don't have the old library, because it was stored on the iMac itself and you don't have a backup, then you will need to create a new library. Use the same option-start-Music method to create a library, save it in <External>/Music, move your existing iTunes Media folder inside <External>/Music/Media and then use File > Add to Library to bring in your content.

You can repeat similar steps as above to get video content into the TV app. Audiobooks & Books can be added to the Books app, but they will get copied into a hidden library folder.

tt2

Thanks tt2!!

I have iTUnes Library.itl - it is less than 4 Mb.

How do I convert it to the new Music Library.musiclibrary format?

Also, I created a new library on my external, moved the existing iTunes Media folder inside it but was not abe to find File>Add to Library option. Do I do that in finder or in Music?

Press and hold down option as you launch Music. You should get a prompt to choose or create a library. Click choose, open the .itl file, and choose a location to save the converted library.

File > Add To Library... is a menu option in Music.

tt2

It 'looks' like my songs are in Music, however, when I click on a song I get the same message "The song XXXX could not be used because the original file could not be found. Would you like to locate it?

I then have to click to the path to the external drive. Do I have to do that for each of my songs?