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I'm a simple man. I want to take the CD my son got in kindergarten. Rip it into mp3/aac using my iTunes 11.3 El Capitan based Mac. Plug in my Son's 5th gen iOS 9,2 based iPod Touch. Put the ripped music into his on device's Media Library. Plug the device back into the stereo in his room. Play the good vibes and see him go crazy the toy drums once more.

Alas, Apple broke that:

Some of the files were not copied to the iPod "Adam's iPod touch" because iCloud Music Library is enabled on this iPod.

This in itself is wrong, as I did enable the family package of Apple Music and added my Son's device into my Apple Music account (streaming of music works on his device).

So now I have the newly ripped music claimed by Apple Music and uploaded to iCloud (fine, whatever). The problem is can't move the files to my Son's device AND I can't share my own uploaded media using something I would imagine be called "Shared Family iCloud Music Library".

The music itself is merely uploaded, not matched and not DRM protected.

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enter image description here This all comes down to me not knowing of a method in which I can put my ripped music on my son's iPod. Which makes it NOT OK any more.

Any suggestions?

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So, I assume the issue here is that physical media you own / purchase doesn't fall under the same licensing agreements that Apple has with artists that allow sharing of their music across multiple devices. Given that... you'd likely need to rip the music using your son's apple ID, so that it is associated with him (and not you) and can be put on the phone. I'm guessing here... which is why it is not posted as an answer. – Charlie74 Dec 17 '15 at 23:54
    
@Charlie74 please see me updated q, this music status is Uploaded. It is not matched / DRM protected thus I can't think of a reason why it not allow me to do the copy to iPod process (as I've been doing before Apple Music using the exact same flow). – Maxim Veksler Dec 18 '15 at 10:33
up vote 0 down vote accepted

As I suspected, once you turn iCloud library on, it is reluctant to allow you to add music using iTunes alone, as there could be file duplicates and a storage war.

Per Apple's forums, turning off iCloud musing will allow you to sync music manually, then you can turn it back on. Note this will delete all the 'iClouded' music and then re-download it, you you'll probably want to do this when you have a spare hour or so and a stable wifi connection.

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Sad to accept this as the best solution. I've done this but it didn't download the trackers. I had to go and manually choose "make available offline" for the 10s of albums I have enabled on that iPod. Also, upon activation the Music app offered to "merge" or "override" the current library with the Apple Music one, this is obviously not a very good solution for common folks. – Maxim Veksler Dec 21 '15 at 10:23
1  
Agreed it's not ideal. Apple is in the middle of a paradigm shift and they could have handled it more gracefully. Glad you were able to finally move the music, though! – agentroadkill Dec 21 '15 at 12:28

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