Migrate iTunes/Music from Monterey to Sequoia

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Level 2

165 points

Migrate iTunes/Music from Monterey to Sequoia

I have a significant music collection, including playlists, on my Macbook Pro (Monterey) that I want to import to my new Macbook Pro (Sequioa); over 9k songs.

I copied the entire directory structure of iTunes over to work with. Including the ~/Music/Music folder.

I've not had any good results.

I need/want to preserve my entire collection, which isn't just iTunes music, but private music files that I have collected over the years, along with the respective playlists.

Is there a reliable way I can do this without having to start all over?

MacBook Pro (M4)

Posted on Nov 12, 2024 9:04 AM

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Answer 1

turingtest2

Level 10

274,552 points

Nov 15, 2024 3:53 AM in response to Forrest

I agree that the error messages are less than helpful. Playlists work with absolute paths. If there is some discrepancy, such as the volume name or the name of your user profile folder then they are going to fail to import correctly. But you really shouldn't be exporting and importing lists in order to migrate a library. Take another look at Managing your Mac media libraries - Apple Community. ~/Music/iTunes/iTunes Music is a legacy location for the media folder. The default name changed to iTunes Media with iTunes 9 back in 2009. With the Music app introduced in macOS 10.15 Catalina the default media folder is ~/Music/Music/Media. If you carefully rearrange the library on the source machine into the now standard layout then it is likely to transfer more easily to a new computer.

tt2

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Answer 2

turingtest2

Level 10

274,552 points

Nov 12, 2024 12:02 PM in response to Forrest

If the paths match on the two systems and you option-start-Music to explicitly select the Music Library.musiclibrary package that you've copied over then it should all work. If you attempt to convert the old .itl again file then the results would be unpredictable.

See Move your iTunes/Music library to a new computer - Apple Community and Managing your Mac media libraries - Apple Community. It may make sense to reconfigure the library on Monterey into the modern layout before cloning the resulting library to Sequoia.

tt2

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Answer 3

Forrest Author

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165 points

Nov 14, 2024 6:53 PM in response to Forrest

So I'm seeing another issue. On Monterey, the Files setting is configured to ~/Music/iTunes/ITunes Music. There is a separate ~/Music/Music directory that has some other newer databases, that must have been configured from subsequent updates.

But, when I copy all of this over, it still doesn't work correctly. Further, I see errors like this:

I don't believe this should happen, all of my music is under one location. Unless, Apple Music app is doing things underneath that I'm not are of when music is added, perhaps with subsequent app updates and the new ~/Music/Music structure that co-exists with the ~/Music/ITunes/iTunes Music folder. Seems kind like we have some disconnection here or that this should really be unified under one folder.

An error like this is not helpful if it doesn't actually show me the files that it's having an issue with, as I cannot understand what the error really is or resolve it.

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Answer 4

Forrest Author

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165 points

Nov 12, 2024 9:13 AM in response to Forrest

Now, unfortunately, there seems to be changes to Music.app that stores more config data elsewhere. Even though ~/Music/Music is now empty, the Music.app thinks there is content. How can I 'reset' the Music.app reliably?

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Answer 5

turingtest2

Level 10

274,552 points

Nov 12, 2024 12:04 PM in response to Forrest

Forrest wrote:

Now, unfortunately, there seems to be changes to Music.app that stores more config data elsewhere. Even though ~/Music/Music is now empty, the Music.app thinks there is content. How can I 'reset' the Music.app reliably?

It is a Mac. Deleting files doesn't necessarily stop them being accessed from the trash until you empty them.

tt2

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Answer 6

Forrest Author

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165 points

Nov 12, 2024 7:11 PM in response to Forrest

Pointing to the Music Library under ~/Music/Music seems to work. But, it does not include the playlists.

So, I did an experiment. I exported a playlist of songs that are contained in this library from my Monterey Macbook and imported it via the Music app on Sequoia. One song will not play, says it can't be found. Hm. So more digging and the *.m4a file is indeed there, it plays fine through the Finder. I can actually find the song in the Songs area, but it won't play through the Music app.

Interesting.

I believe this song is imported from one of my CDs I have... I have 100s of similar songs that I use in iTunes like this.

So I am now wondering if there are going to be more similar issues like this with the Music app.

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Answer 7

turingtest2

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274,552 points

Nov 13, 2024 1:08 AM in response to Forrest

Playlists are stored within the Music Library.musiclibrary package. If you migrate the library correctly they all come over too. If you export a playlist and then import it into another library you may find some songs are not added back to the list. This can happen if the track isn't at the exact path specified. Various diacritical marks may get badly handled during such a round trip.

tt2

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Answer 8

Forrest Author

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165 points

Nov 15, 2024 8:22 AM in response to turingtest2

Thank you, this is very helpful. So on my older Monterey (Intel) Macbook Pro, I have a mix of the iTunes and ~/Music/Music directories and databases. I know that new music is being written to the iTunes portion of this, as I regularly back up my music (the actual songs) when I add more (and I see the xfers).

I copied all of this over to the Macbook Pro M4 (Sequoia), but as I mentioned it's not been working reliably. I wonder if there might be a way to "fix" this on the Monterey side first, which might make the migration easier? I even asked ChatGPT, which wrote some Python code for migrating, tho I don't really trust it :)

I am very comfortable on the CLI (I'm a sysadmin), but it doesn't appear there are any tools to interact with the Music libraries, etc., and the databases may be in a proprietary format, which would make it even more challenging.

There is a "Sync Library" function somewhere, if you subscribe to Apple Music (I do not) -- which doesn't really help me here. Would be great if that were just a general part of the OS, it would help a lot here.

Are you aware of any CLI tools I might use. I am not sure which parts of the structure the Music app is using, on Monterey, under ~/Music/Music and ~/Music/iTunes.

Thanks!

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Answer 9

Forrest Author

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165 points

Nov 15, 2024 8:59 AM in response to Forrest

I am not familiar with the new Music/Music structure or what is going on, but the files I have are:

-rw-r--r--@ 1 me  staff     9358 Apr 27  2021 Application.musicdb
-rw-r--r--@ 1 me  staff    16384 Apr 23  2021 Extras.itdb
-rw-r--r--@ 1 me  staff    32768 Jul 29  2019 Genius.itdb
-rw-r--r--  1 me  staff     1362 Apr 27  2021 Library Preferences.musicdb
-rw-r--r--  1 me  staff  6845492 Apr 27  2021 Library.musicdb
-rw-r--r--@ 1 me  staff      124 Apr 23  2021 Preferences.plist
-rw-r--r--@ 1 me  staff        8 Apr 27  2021 sentinel

I presume these database files are in some non-standard, proprietary format. But do we know the relationship between these and the legacy iTunes folder/db/structure which is clearly still being used? I note that these don't appear to be updated. Whereas my iTunes folder is where updates are taking place.

I think creating a structure that has things all over the place like this is confusing and could be make more uniform.

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Answer 10

turingtest2

Level 10

274,552 points

Nov 15, 2024 10:14 AM in response to Forrest

I've just checked the .musiclibrary package on my M1 MBA. The package date shows the original creation date of 2020, but if I open the library and make some changes all of the internal files are updated with today's date. You have somehow copied over the wrong .musiclibrary package. There must be another somewhere on the Monterey system. In general there is no need to dive inside this, the files are not meant to be used by anything other than the Music application. Try holding down Option as you launch Music and tap the Choose Library button. It should present you with the location of your active library. This is the package that you need to copy to Sequoia, then access by holding down Option again as you launch Music.

tt2

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