Music syncing only purchases, not full library, to iPhone

It seems like my post and iTunes Original File Could Not Be Found - Apple Community are related, however running Version 1.0.1.41 of the script did not work. After changing the security permissions in PowerShell to be safe it would work, the VBS file seemed to launch fine and I followed the prompts as instructed.

However running the script put it in what appeared to be a loop, or was individually showing an error message for each individual track which appeared once every ~3 seconds. Here are the 2 error's shown on repeat:

I was only able to escape the loop by exiting from iTunes, which then showed a different error:

I can confirm that each of these non-playable tracks are referencing the album folder, not the actual track file, as the location iTunes song info shows:

C:\Users\_\Music\iTunes\iTunes Media\Music\Aimee Mann\@#%&_! Smilers

Instead of what it should be:

C:\Users\_\Music\iTunes\iTunes Media\Music\Aimee Mann\@#%&_! Smilers\05 Borrowing Time.mp3

Another file example that plays correctly, and syncs to my device correctly, references a file location of:

C:\Users\_\Music\iTunes\iTunes Media\Music\Animal Kingdom\The Looking Away\02 Get Away With It.m4a

And to confirm once more, the iTunes library as selected under system>advanced preferences is:

Update: I have created a ticket with Apple Support, Case ID: 102564756894. So far I've spoken to 6 different tech rep's (so far), 3 of them senior, none of whom have been able to diagnose the problem. We can only confirm that the problem with syncing music to my device happens with iTunes and with Apple Music/Devices, and that both applications are referencing the correct library file locations for each song.

By chance I noticed that the songs which are not syncing are mostly MP3's, downloaded from many other sources such at 7-Digital, SoundCloud, Bandcamp, or directly from an artist's website. These songs were all organized correctly in iTunes before, complete with album artwork and details. The music library continues to organize these songs into their respective playlist correctly, but the songs themselves do not play from within the Apple software. There is no problem with song playback if I open the file directly from Windows Explorer/Finder, and play using VLC player or Windows Media Player; so we can confirm that the song file is not corrupt in any way. Here's one example:

The bottom song is the original MP3 as the library playlist has saved it, located in the correct file folder. The top song I simply drag-dropped the same exact MP3 into the playlist window again, and now it shows all the album artwork/details again. It also moved the file location from 'C:\Users\_\Music\Apple Music\Media' to 'C:\Users\_\Music\Apple Music\Media\Music' automatically, despite me not having that setting selected.

So new problem hypothesis: the songs which are not syncing to iPhone are all similar to the above example; they cannot be played in any Apple software until the exact file is re-imported into the library.

Obviously I do not want to go song by song through +6000 files to re-import into a library, which already appears to be organized just fine. Because these songs had no playback or syncing problem in previous software versions, this seems like an obvious bug Apple needs to address. Barring that long process of software development, what can I do now to make these songs read correctly (en masse)?

Just for good measure, I repaired the security permissions as you suggested. I also re-installed iTunes directly from Apple (which, FYI, contradicts Apple's own tech support recommendations to download from MS-store or use Apple Music instead). iTunes works better than Apple Music so I'm happy to revert back.

You are correct, the songs will still not play within iTunes, despite the library (seemingly) being organized correctly. The same issue exists where file locations are 'found' correctly from within iTunes, confirmed by selecting any file and "showing in windows explorer". A song file location matches the parent library folder location as defined by iTunes' settings: C:\Users\_\Music\iTunes\iTunes Media\Music\[artist folder]...

I do not use OneDrive or any other cloud drive service; all music files are saved locally per the default folder locations.

I would be interested to try a script to fix broken links, if you think this is most likely the issue. I also would be interested in repairing the ID3 tags as suggested in your earlier link, but iTunes has that option greyed-out for me, presumably because it's still confused about file location.

Thanks. Your direct link to v1.0.1.42 worked, but the one from the website still shows the old version.

I ran the script on 2 playlists to test:

For the one which claimed 5 files were updated, because it does not show me which ones I cannot verify the script did its job, so I ran the script again on the much smaller 4-song playlist next.

For all these non-updated songs the same issue persists; iTunes thinks the track file is located in the correct ALBUM folder, but it needs to look one level down (into the ALBUM folder) in order to see the actual track file.

I changed the code in Visual Studio, line 151 only, and saved a new script file. Running produced varied results; most files were not updated, but some were correctly. I tried several different playlists to test and overall, the script seemed to work only 1% of the time (compared to the # of tracks it was trying to resolve). Here is the only example of a somewhat-successful run:

What's perplexing is the tracks which were successfully updated with new file locations all had the same issue as any other problem track: iTunes needs to look one level down into the album folder to find the correct file. Even more perplexing is when I validated the 6 tracks here which were updated, I noticed that none of them had ID3 tag information for album, genre, etc (shown below in green). Tracing back what it did, the script worked to create a new "unknown" album folder for each respective artist, then placed the track file in that new folder. For all other tracks that already have an existing/named album folder under each artist, the script did not work.

Version 1.0.1.42 - April 15th 2025
_
Dim MatchFirst          ' Take first match when the is more than one
Dim MoreInfo            ' More dialog boxes to reveal state of processing
Dim ArtistTitle         ' Option for alternate layout
MatchFirst=True
MoreInfo=True
ArtistTitle=True
SkipLost=False
SkipMulti=False
_

I agree, iTunes was a far easier experience to work with than Apple Music, but it was a forced upgrade from Apple so iTunes no longer works to transfer music files to devices (at least using Windows OS).

The issue still persists.

Unfortunately uninstalling Apple Music+Apple Devices did not work. Opening iTunes after that process and connecting my phone only showed a message saying that downloading the new Apple software was necessary before continuing.

I also tried some different sync settings within Apple Devices which did not work. Removing all theoretical restrictions I opted to sync my "entire (56Gb) music library" to the phone so there should not be any reason why one playlist or individual song would be left out. Still however, only 5.4Gb of audio is being transferred over.

Not sure what I should try next here, because I can confirm Apple Music contains the correct song content I want to transfer, and Apple Devices sync settings are seemingly selected properly to transfer my entire library, yet it still does not.

Per your advice on Apr-8, the current build of iTunes on this machine is v12.13.7.1, downloaded directly from Apple. Prior to that install, I had downloaded iTunes, Apple Music, and Apple Devices all from the Microsoft Store (all resulting in the same syncing problem).