Apple Music on Windows is only syncing my purchased songs, not my entire library

I just started using Apple Music on Windows 11, transferring over from iTunes. When attempting to sync my music library for the first time using Apple Devices, only songs which I've purchases through the iTunes Store seem to be transferring over to my iPhone (exactly 138 out of 6341 songs). I have made sure all checkbox's and sync settings are correctly selected, and ensured there is adequate SSD space on my phone device, however this changes nothing and the problem persists.


Interestingly I notice that certain settings, [manually manage music, movies and TV shows] and [sync music onto (device)], become unchecked after I select to apply settings and re-sync the device. I can go back and re-check these settings, either individually or simultaneously, and every time without fail, these are automatically unselected again following a device sync and my music is not correctly mirrored.


Is there a phone settings conflict which is causing this, or security permissions? How can I get my music to sync properly?



[Re-Titled by Moderator]



iPhone 14 Pro, iOS 18

Posted on Mar 14, 2025 3:17 PM

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Posted on Apr 8, 2025 1:06 PM

I'm assuming the songs that don't sync still play in the library? Did you try anything similar to Repair security permissions for iTunes for Windows - Apple Community, i.e. explicitly reapply the default security permissions for all files within the media folder?


I haven't had a chance to test it, but at least one person has suggested that the latest Microsoft Store version of iTunes for Windows may not revert properly when the other apps are removed. Removing that and reinstalling iTunes from this link might help there: https://www.apple.com/itunes/download/win64.


The extra Music folder inside the media folder is standard. If you copy something into the media folder, or it starts off inside it but the Keep organized option is on, then iTunes/Music will use their layout rules. iTunes 9 introduced iTunes Media Organization which added a subfolder for Music in the media folder into which artist folders would be put, to match the existing high level folders for other media types. Now that Apple Music is focused only on Music this extra layer is unnecessary, but Apple didn't think to change the default library layout to exclude it, or provide a way to remove it. (You can still add it though if it is missing, at least in the Mac version.)


If you were running iTunes I could offer a script that could potentially fix any broken links, but Apple Music is lacking support for such niceties.


Is there any redirection going on with your Music folder? Not buried in OneDrive or something? The right hand screenshot above doesn't show the full path, but what is shown appears to agree in all the visible components. In principle iTunes/Apple Music won't reimport a track when there is already one in the library with the same absolute file path.


tt2

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36 replies

May 31, 2025 11:03 AM in response to turingtest2

Hi there,


Thanks for sending over those files. Really helpful. Sorry it has taken me a few days to come back to you.


I picked a few albums in your collection that I also have in mine, converted files to the same format as yours, massaged the filenames to match yours, e.g. mostly no leading track numbers, and set the folders out in the same layout. Took a little while to reverse engineer the intent of some of the blocks of code that I haven't touched in ages, but I've got things to the point where it should reliably search the already known folder (as per your oddly broken tracks) and select the correct file from within it, particularly if the found file matches the size of the original. My test files weren't the correct size, but could be made to match and would do so in a batch without confirmation if needed. I'm sure there is more that can be done to make it better, but I think there should be some progress at least this time. Please let me know how you get on, and share examples of any specific tracks that don't get relinked. The Japanese(?) characters on the Cowbow Bebop album may present at issue, and any unnamed tracks are obvious potential points of failure, but hopefully those won't be too hard to mop up once the bulk are fixed.


tt2

Jun 2, 2025 9:50 AM in response to turingtest2

I see no new results using Version 1.0.1.45 than with v...44. Though I am starting to use it with larger playlists regardless, just to identify specific problem tracks.

Of one of the un-updated track examples which is stated as "missing," iTunes' song info lists the correct file path location but still will not play. If I select to manually locate the file as prompted, iTunes strangely takes me to a system directory as it's default location: C:\Windows\System32.


As far as I can tell, anytime the script runs and states there are missing tracks, all of these tracks are from a compilation album of "various artists". As with the song example above, I can go through each one and confirm that the iTunes song info correctly displays the track file location, but iTunes also still still thinks the track is still missing and requires to be located.

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Apple Music on Windows is only syncing my purchased songs, not my entire library

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