Apple Music v iTunes on Windows 11

I upgraded my Microsoft PC from Win 10 to Win 11. Since then iTunes has lost the links to my music files, there does not seem an easy way of re-establishing them apart from album by album. With a large collection like mine this is very tedious. So I have started to think perhaps I should move to Apple Music and give up on iTunes. Here are a few questions:

How do my music files link to Apple Music or do they?

Is it neccessary to link the music files on my PC to iTunes/Apple Music?

What will happen to my iPod Classic if I try and sync it now with music files disconnected?


Windows, Windows 10

Posted on Apr 27, 2025 4:41 AM

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Apr 27, 2025 6:17 AM in response to alan from hemel hempstead

If iTunes is broken then installing Apple Music will either result in a similarly broken library, or an empty one. Once Apple Music, Apple TV, or Apple Devices are installed then iTunes is limited to managing audiobooks and podcasts. Don't go down that route. Apple Music is much less capable than iTunes.




The "missing file" issue with exclamation marks happens if the file is no longer where iTunes 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, or the drive it lives on has had a change of drive letter, 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 has 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. See Getting iTunes & Windows Media Player to play nicely if you're trying to access your media with any other media players.


Select a track with an exclamation mark, use Ctrl-I to Get Info, then click No when asked to try to locate the track. Look on the file tab for the location that iTunes thinks the file should be. Now take a look around your hard drive(s). Hopefully you can locate the track in question. If a section of your library has simply been moved, a folder renamed, or a drive letter 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 Windows.


In some cases iTunes 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 another application like Windows Media Player has moved/renamed the files, or the library has been moved from OS X to Windows, then the chances are that subtle differences in naming strategies will make it hard to restore the media to the precise path that iTunes is expecting. In such cases, as long as the missing files can be found somewhere, you should be able to use my FindTracks script to reconnect them to iTunes. See this post for an explanation of how it works. It might need some tweaking if your media is in a non-standard layout.


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

  1. The location of the media folder under Edit > Preferences > Advanced
  2. The location of a sample missing track shown under Get Info > File > Location that begins file://localhost/
  3. The true path to the file whose details you gave in 2


Note the addition of file://localhost/ (and the flipped direction of slashes in Windows) is normal for a file that isn't quite where iTunes is expecting to find it.


tt2

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Apr 28, 2025 9:18 AM in response to alan from hemel hempstead

I think I understand. You have an Apple Music subscription, and have somehow moved over the media but not the library. On opening iTunes and signing into your account you are now able to access your iCloud Music Library, which isn't aware of any local tracks. It might be possible to revisit your old computer and my user tip Move your iTunes library to a new computer - Apple Community if you want to bring over the old library database. Otherwise you should be able to import your local files, and iTunes should merge those with the items in the cloud so that it can play your local files thereafter. I would suggest testing behaviour with one or two albums to start with to make sure that, for example, date added is preserved once any duplicates are eliminated. You may need to close and reopen iTunes to clear cloud duplicates, or perhaps even sign out of the store and sign back in.


As far as you classic is concerned you can only sync locally stored items to it, you cannot copy content that is in the cloud. You should also maintain a local copy of your files in case anything is removed from the Apple Music catalog, or you decide to cancel the subscription.


tt2

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Apr 28, 2025 12:57 AM in response to turingtest2

Thanks for this helpful information. I have looked further into the issue, if there is one, and will explain further.


Previously under Windows 10 all albums were downloaded to my PC and played from the hard drive. Upgrading to Windows 11 has broken that relationship. Every album is now showing with a Download symbol in iTunes, which was not there before. I cannot see the exclamation mark you refer to.


If I select to download an album and then look into the hard drive folder I now find every track appears twice. So iTunes is downloaing to the correct folder but does not seem to realise the album is already there.


I seem to be able to play albums without downloading them, so I am wondering what the advantage is of having them on my hard drive anyway.


I am still unsure what will happen if I plug my iPod Classic into my PC but I am wondering if I need to going forward. I seem to be able to cast tracks from Apple Music on my iPad to my Hi-Fi sytem over Wi-Fi so why do I need anything esle?



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Apr 29, 2025 11:51 AM in response to turingtest2

Thanks, I have backed up my albums using SyncToy. I have checked in Edit / Preferences / Advanced and iTunes is pointing to the correct folders where the albums are held. However in my Library each album is shown with a download button suggesting the local data is not recognised. Previously in Windows 10 the download button was not there and all tracks where played from the hard drive not the cloud. I cannot see a way of forcing iTunes to do this in Windows 11, apart from deleting the current tracks and downloading them again. This could take years.

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Apr 30, 2025 6:44 AM in response to alan from hemel hempstead

I have now found a way of getting iTunes to recognise the albums held on the hard drive by re-pointing the application to the folder. However this did not work for all tracks and a large amount of time has been spent going into every album to correct any anomolies. This took me five hours in total. I don't remeber any warning about this happening when upgrading from Win 10 to 11!

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Apple Music v iTunes on Windows 11

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