So I've made a new playlist and it seems to work fine until my iPod syncs. Then I get messages that several songs cannot be found so they don't remain on the playlist. I do not see how to fix this.
Mac mini, macOS 12.3
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:
See also FixLinks - an AppleScript to repair broken links in Music - Apple Community.
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:
See also FixLinks - an AppleScript to repair broken links in Music - Apple Community.
tt2
It seems you've probably turned off the option to Copy files to the media folder when adding to the library and have added content directly from USB drives, or moved (rather than copied) it there after adding to the library. This content will then only work correctly when the drive is connected, and perhaps only after repairing a broken link. All your media files should be stored in the media folder so they are there ready to be played when you ask for them, or synced to your device when needed. If you connect each of your USB drives in turn and use File > Library > Organize Library > Consolidate Files, Music will be able to copy in those tracks which are broken because you removed a drive after import. Where you've actively moved the files you either need to repair the link and then consolidate, or manually copy the items to the expected path as shown under Get Info > File tab.
tt2
Thank you for the reply. I saw your post from awhile back and have tried to work my way through it. First off the media folder is not under advanced but under files and looks like this..../Diane/Users/diane/Music/iTunes/iTunes Music/Mettaverse Music/Unknown Album. It took me awhile to find the song file....file:///Volumes/DIANE 5/04 My Strongest Weakness.m4a. So I went along this path....HDDiane..(from this point to the song it's all folders) .Users...diane...Music...iTunes...iTunes Music...ynonna Judd...Wynona...the song! I can play the song from this final point. Ugh!
These missing songs are very few which I don't understand as I make a lot of playlists and usually don't have an issue. Why just a few songs?
I suspect the issue is happening because I transfer music to USB drives. Then when I hook the iPod back up to iTunes/Music it updates and the problems ensue. Only on some songs though. For example: I purchased one song and saved it to a playlist. I added the song via copy/paste onto the USB. I then saved it to another playlist. So it's now on two playlists so it shows up twice in the Songs area on iTunes. One of the two is marked with and exclamation point. Actually I just noticed that this is the same for the song I have traced above. Perhaps I'm making my playlists incorrectly or transferring to the USB incorrectly...I've never found info as to how to do that correctly.
I am running current versions of everything...I certainly do not understand all of this so I appreciate your willingness to help. I've actually considered deleting the playlists with the songs in question and starting over.
Wow! Well I turned on the Copy files part. I only take music to USB not from. I played around with it yesterday and deleted one of the songs with the !. This song had two listed in Songs, one with ! and one without. Then I used the add to playlist and put it back in that particular playlist and it seems to work as it now shows up on my iPod. Fortunately I only have maybe a dozen in question. My next thought is to wipe all music off my iPod and then sync it and see what happens. I've had a lot of problems with Music...not syncing, not syncing between devices etc. Apple had me do stuff I do not understand and cannot do again without help. Now at least my phone seems to sync.
Can you tell me the appropriate way to take my music to usb? The cd transfer is easy but maybe I'm doing the usb part incorrectly. I usually hit select all in a playlist and then just paste it into the usb...not in folders...that didn't work...but as songs. But they never copy over in the exact order...they go over with their track numbers in order. Not the way I want it.
Thank you very much for your help. I think I understand it a bit better.
Sorry I forgot to get back to you on the USB export. There isn't really a simple way to do it from Music and have the tracks export in a pattern that puts them in a specific order. See https://dougscripts.com/apps/m3unifyapp.php for a tool that might work the way you want.
tt2
Some songs "cannot be found" on making playlists
