Moving iTunes from Windows to Music App on Mac

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hoopythemuggish

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I’ve had PCs for 25 years but now have Apple gear bar a MacBook - IPhones, iPads, iPods, Apple TVs but am now sorely tempted to splurge on a 16 MacBook Pro but have been unable to find any info on how to transfer my iTunes library over whilst retaining all the metadata especially playcounts as my smart playlists dictate my listening habits. I hated moving my library from an old laptop to a new laptop and the whole process always fills me with dread as only once did it work first time.

I don’t particularly think iTunes is very good compared to other music management software but is the only one that plays nice with all my Apple gear and does what I need it do despite it being buggy from time to time on both my laptop and iOS devices.

If I can’t move the library across easily I may to have consider abandoning Apple altogether but the options around don’t quite fit how I listen to music. I’d never consider streaming as I have a carefully curated 25000 song library
 

cjmnews

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With the new 16" MacBook Pro, you will be on Catalina OS, where iTunes does not exist. It was replaced by the Apple Music, Apple Podcasts, Apple Books and Apple TV apps, plus a Finder based sync mechanism. I have not found a way to use it on an external drive yet, if you have a large library this may be a necessity. I can research if needed.

I don't have Catalina yet. so I have not needed to do this but have been reading a lot of posts about the migration. Though you are probably a pioneer in this, as most of the post I am seeing are migrating from Mojave to Catalina (Mac to Mac) not Windows to Catalina.

With all the smart playlists, I assume they are in folders. The current Catalina Music App has a bug with folders, as it creates a "Smart Playlist Folder" smart playlist for each folder. Some people say they have lots of tracks in them, others say there is nothing in them. I think the lots of tracks people had normal and smart mixed in the folders, where the empty ones were all smart playlists. They say to delete the folders, and just have a list of hundreds of smart playlists. I think this bug alone would stop my migration.

First off, make sure all of your music is in the iTunes folder (.../users/<login>/Music/iTunes/iTunes Media). If it is scattered across your hard drive in many folders, you should Consolidate your library. This will ensure you get everything at once. This is in File->Library->Organize Library, check the box called Consolidate files and click OK.

Copy the whole iTunes folder to an external hard drive. This assumes your library file (usually named iTunes Library.itl) is in the iTunes folder as well. If not, you need to copy it separately to the external drive.

On the Catalina system, you should have a ~/Music folder. Copy the iTunes Library there.
Then copy the iTunes Media folder into the ~/Music folder
Then hold the Option key and start Music app, select the iTunes Library.itl file and save as Music.

That should get your music with all metadata and playlists into the Catalina Music App.

If something is messed up, we can erase what was done and try other steps with the external backup.
 

hoopythemuggish

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I almost bought the MacBook today as there was a 10% discount on a UK website that the local Apple Store we’re prepared to match and then found they couldn’t and then we’re going to give me £160 of vouchers which I figured I’d use on dongles and the like until they decided the promo didn’t include the 16. So I didn’t get it and will probably wait till January now I know they price match.

As regards the migration, smart playlists can be recreated if necessary but the playcounts, date added and ratings really matter as they dictate what’s in the playlists. Everything I have is inside the iTunes folder so I don’t need to consolidate. I also back up regularly to an external hard drive, is it better to use this rather than iTunes folder from laptop?
 

cjmnews

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All of the metadata should make it, along with the smart playlists using the Option+start Apple Music app method and importing your library.

Using the backup vs a copy of the iTunes folder is dependent on if you use special software for backups or just copy the folder. If it is just a copy of the folder and it is recent, then the backup is fine. If you have the same software used for backups to restore on the Mac, that would work too. Most people that post here have no backups.
 
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