Moving iTunes library from Windows to Mac using the Music.app

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Moving iTunes library from Windows to Mac using the Music.app

I have followed advice on moving a Windows based iTunes music library from Windows to the Music app on MACOS - especially as set out by the helpful turingtest2 who I'm hoping is tuned in - but I am having problems.

My music files are well ordered in a single folder. I've attached a screenshot of the folder structure I copied over from my Windows system (the library was on its own separate F-drive). Everything related to the music library is in a folder called LIBRARY-MUSIC. This folder includes an iTunes folder (with the iTunes Library.itl file, and related xml file). All the media (music files) are in another folder called MUSIC.

I start Apple Music holding option. It asks me to choose a library. I select the .itl file (Library-Music/iTunes/iTunes Library.itl). It then asks me to choose a folder for the library file (Music Library.musiclibrary) the app wants to create. I put this in a new folder I called Music_LIB.

When the Music app starts, it includes all my music files, songs, albums, ratings, playlists but none of the songs are linked - the file paths are broken. It also doesn't show album artwork. What should I do to ensure the file paths work as expected by the library? Is this something to do with where I place the new Music Library.musiclibrary the Music app forces me to set up? If that's the key, where should I put it?

Feels like I'm so near and yet so far. Grateful for any advice that can help me fix this problem. BTW, I'm using a new Mac Mini M4 with 24gb RAM on Tahoe.

[Edited by Moderator]

Mac mini (M4)

Posted on Oct 2, 2025 12:42 AM

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Answer 1

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turingtest2

Level 10

277,949 points

Oct 2, 2025 3:40 AM in response to superspecific

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. I think the app needs to be "aware" that multiple tracks are missing before you attempt to fix one, in order to trigger the offer to automatically fix others.

If you want me to try to provide specific advice please post back the following details:

The location of the media folder under iTunes|Music > Preferences > Advanced
The location of a sample missing track shown under Song Info > File > Location that begins file://
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.

A quick look at your screenshot suggests you have a lot of legacy cruft in the iTunes library. Music won't use the Windows Album Artwork cache, iPod Games and Mobile Applications are things of the past, and the media folder would have been better renamed as iTunes Media while you were still working on Windows. See also Managing your Mac media libraries - Apple Community.

tt2

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Answer 2

Oct 2, 2025 5:14 AM in response to turingtest2

Hi turningtest2, thanks for this helpful reply. Your suggestion of looking in the SETTINGS/FILES was a winner. I pointed this setting at the MUSIC folder highlighted above and the all songs linked perfectly (image attached). That part is now fixed.

My remaining issue, however, is the album artwork. You say Music won't use the Windows Album Artwork cache which stacks up because none of my songs/albums display artwork despite the fact the files are all tagged with the appropriate artwork and that I've also set my view options to always show artwork (see screenshot). I've read your Managing your Mac media libraries post but although this confirms the Album Artwork folder is now redundant, it doesn't appear to say what replaced it (hope I didn't miss something). Do you have any tips on that element - how I can get the Music app to show the embedded artwork?

Also, thank for clarifying the situation with iPod Games and Mobile Applications, etc. I don't use them and can delete in due course, but will first focus on getting my music library working as it did under Windows.

Thanks for taking the time to steer me in the right direction and I'd be grateful for any advice you can offer on the artwork.

[Edited by Moderator]

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Answer 3

Oct 2, 2025 5:35 AM in response to superspecific

For clarity, I would add that when I say the artwork is embedded, it shows up in Finder and when I play a song file on an app like IINA. I would routinely add artwork to song files along with clean tags before uploading the files for iTunes on Windows.

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