Macbook refusing to transfer music to iphone

This is the method you should use when you do not have a subscription to Apple Music or iTunes Match: Use the Finder to sync your iPhone, iPad, or iPod touch with your Mac - Apple Support. It uses Finder rather than the Music app, although it connects to your active Music library. I would recommend syncing with selected playlists (or all of them) rather than manual management.

If/when you have a subscription to either Apple Music or iTunes Match you would typically enable Sync Library (aka iCloud Music Library) in both your computer and your device so that all content is added to a cloud library that syncs automatically between devices. You can check the iCloud Status column in the songs view of the library to look for items with issues, e.g. waiting, error, etc. If you have those post back and we can discuss how to resolve.

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To sync directly from the computer Sync Library needs to be turned off on the device.

See also If you have music that won't play on your device - Apple Community. You may need to clean up/reset the Music storage on the device before you can successfully sync content back to it.

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rattleheaduk wrote:

I have stored my music on an additional drive for years, should I wish to change music on my phone (Iphone 14), I hook up the drive and go.

I've just re-read this comment and I'm sure it is pertinent. With iTunes you could connect your drive, fire up your library, and sync with it. Finder appears to attach to a cached copy of the Music library when Music isn't running. This means that you can sync without launching Music, but if your media library isn't attached and connected to your computer when you start the machine Finder may well detect that the media is missing, and then not necessarily re-evaluate things when the time comes that you want to sync, even if you have by then attached the drive.

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rattleheaduk wrote:

Is there any point deleting/reinstalling music on my mac rather than my iphone, which I've already tried?

I don't think so. At this point the suggestion I make in the user tip may be relevant:

If the method above has not worked for you then a more comprehensive approach is to backup your device, restore as a new device, then restore your backup.* All of your media that you want to restore to your device must be in your library before you try this. You should ideally backup your device to both your computer and iCloud in case one of the backups doesn't work when you try to restore it.

* After which you can select music to sync to it.

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rattleheaduk wrote:

I moved all the files to a new location.

Why? Editing the media folder location in preferences tells Music where you want new things to live in future, it doesn't expect you to move content that has already been connected to the library.

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.

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See Managing your Mac media libraries - Apple Community and the section on iTunes Media Organization. Either you need to create the expected Music folder, and move all of the artist folder into it, or you need to edit the hidden .Media Preferences.plist file and change the integer value from 1 to 0 so that Music isn't expecting that additional subfolder.

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Here are some screenshots showing the path to my media folder in Music preferences

what Music gives as the expected location for a missing file

(the window can be resized to show more text) and finally using Get Info in Finder to show the path the "missing" track

To make the last two images I first made a copy of the track, then deleted the original immediately so it wasn't sent to the trash, thus breaking the link to the library. I can fix the issue I've just created by removing the copy from the filename, but to analyse your issue I do need to see all of the path details, either via a screenshot, or by you manually copying out the complete paths.

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rattleheaduk wrote:

Is this what you need:

https://discussions.apple.com/content/attachment/36dc15ac-2d01-4a57-b517-ca273de0ae5c

I can't find a method of seeing what those additional 'Music' file types are I'm afraid.

I assume that is what Song Info > Don't Locate > File tab shows. According to an earlier screenshot the media folder location is set to Expansion > Media. What about the actual location of the file 02 Snakes Of Christ.m4a? Find the file using Finder, right-click on it and Get Info to see the full path under the heading Where:.

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rattleheaduk wrote:

I have noticed that the default location sometimes resets if I close the Music app but doesn't do it every time.

This typically happens if you open Music when the external drive isn't ready. Music, like iTunes before it, silently resets the media folder to the default path below the active library. Copying your Music Library.musiclibrary package into //External/ and then option-starting Music to choose the library at //External/Music Library.musiclibrary prevents this issue from occuring. If the drive isn't ready Music says it cannot find the library, in which case you cancel, connect the drive, and open Music once more. No unexpected side effects.

With your library database held on the external drive your Music folder should be set to //External/Media. You should then be able to try locating missing tracks once more, either using Music's own feature, or the script I posted about previously, FixLinks - an AppleScript to repair broken links in Music - Apple Community.

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