Transfer complex iTunes library to iCloud

You cannot use iCloud Drive to store music that can be streamed to your iOS devices or Apple Watch. If you want that facility then you need iCloud Music Library, either with iTunes Match or Apple Music. My approach to this was to create a separate library and gradually add content into it that I wanted to have on my iPhone. That way I was able to add content gradually and make sure that it either matched or uploaded fully before adding another batch.

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Hi Jill,

The most straightforward way to do this is via iTunes Match:

Subscribe to iTunes Match - Apple Support

Apple Music also provides this kind of functionality, among its other features, but iTunes Match is a bargain, relatively speaking.

Cheers

Jill Christiansen wrote:

What exactly would iTunes Match do for songs that haven’t been purchased?

Jill, it can be complicated! You're wise to be cautious and to want to understand completely what's going on.

The first thing iTunes Match does when you turn it on, as you remember from last time, is to scan the contents of your library, which it then tries to "match" with music available in the iTunes Music Store. No matter whether you bought the music from iTunes, or from a different source, or imported it from CDs, or anything, all your songs are handled the same way:

• Songs that can be matched to items in the store are not uploaded to your iCloud Music Library. They'll show up in the Music app of your iOS devices, or the iTunes app of your computers, whenever you log in, and they can be streamed or downloaded as 256kbps AAC (.m4a) files, regardless or what format and bitrate they had originally on your computer.
• Songs that cannot be matched are uploaded to your iCloud Music Library. If they have a very high bitrate, like lossless audio files, they'll be converted to 256kbps AAC while this is happening. As with the other files, these will show up on all your devices for streaming and/or downloading.

From your standpoint as a user, there will be no difference between matched and unmatched songs — you can see them and play them from all your devices. (If you've got a bunch of old 128kbps tracks from back in the day, you can take the opportunity to replace them with higher-quality versions.)

Cheers