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Solve iCloud Music Library Match Problem

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Based on my experience, the Matching aspect of iCloud Music Library (presumably the same logic as iTunes Match) is a disaster. I have a particularly troublesome issue with the uploading of rare live albums.


Like Kirk, I am a huge Deadhead. I’ve got a bunch of rare live box sets like Formerly the Warlocks, Winterland ’73/’77, and Spring 1990 which are NOT available to stream. I therefore figured that I would upload the ripped tracks from these albums to the new iCloud Music Library using the Match feature. My expectation was that all tracks would upload (and not match) since none of them are available anywhere in Apple’s catalog.


When I tried to add all of these tracks to the iCloud Music Library it was an unqualified disaster…some tracks uploaded, some didn’t…live tracks were swapped with studio versions or the wrong version from another digitally available live set (e.g. the “Samson & Delilah” from Dead Set appeared instead of the expected version from Winterland ‘77).


Any suggestions before I give up and just upload all of these tracks to Google Play Music? From everything I’ve read, there is no “force upload” option associated with iTunes Match/iCloud Music Library and Match users have been screaming about it for years.


Sucks to have music in two separate cloud lockers but the Apple offering just doesn’t seem to work.

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There is no more Add to Cloud menu item, as there was before. So there's no way to force uploads.


The fact that it's now matching tracks to totally different versions is new; iTunes Match didn't do that. So, yes, I'm considering what I'll do in the future. Right now, I haven't updated iTunes on my main Mac.

I write about Macs, music, and more at Kirkville.

Author of Take Control of macOS Media Apps

Co-host of The Next Track podcast.

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I gave up on the cloud and tried to simply sync the affected tracks to my phone, store them locally and have them co-exist with the iCloud Music Library on that phone. This worked in theory...but as you have pointed out many times, Apple changes my album artwork which is maddening. Here's what I did:


1. Turned off iCloud Music Library on my iPhone 6.


2. Added the above tracks to my phone via iTunes/the old school drag and drop method.


3. Tracks appeared on the phone with the correct metadata and artwork.


4. Turned iCloud Music Library setting on the phone back on.


5. Tracks are still on the phone with the little offline indicator on them. HOWEVER: totally incorrect artwork is displayed...it's not even consistent for tracks on the same album.


Unfortunately it looks like the call to the iTunes Store overrides any artwork you add to even your local tracks.

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