How to reconnect an iPod Classic to the main iTunes library?

Question

How to reconnect an iPod Classic to the main iTunes library?

I recently had a hard drive failure on my Mac and had to restore my iTunes library from iCloud. Now that I connected my trusty old 5th Gen iPod Classic to my Mac, I got a dialog saying something like "the iPod can't be connected to several libraries" and "do you want to copy your music to the Mac". I then (too hastily) clicked OK. iTunes then did some copying from iPod to Mac. After that the iTunes library I see in the iPod sync view is different than my main iTunes library. I did reset the iPod in iTunes, but I'm still seeing only a part of my iTunes library in the iPod sync window. What do I need to do in order to reconnect the iPod to the main iTunes library so that I can sync music from my main iTunes library to it? My Mac is a Mac Pro (Mid 2010) running macOS Sierra 10.12.6, iTunes version 12.6.2.20.

Screenshot: iTunes library as seen in the iPod view

Screenshot: main iTunes library view

iPod (5th generation), iPod software version 1.3

Posted on Sep 9, 2017 4:30 AM

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Answer 1

Sep 9, 2017 10:08 AM in response to turingtest2

As luck would have it, turned out my TimeMachine backup had died already a month before the HD failure, so there are no usable backups available.

But I don't think CD rips have accidentally become Apple Music, as you suspect.

In iTunes, Apple Music tracks are tagged "Apple Music AAC tracks" and "iCloud status: Apple Music". CD rips (iTunes Match) are tagged "AAC tracks" and "iCloud status: matched". See screenshots below. That particular CD rip (iTunes Match) Santana track nor the album it belongs to nor the playlist the album belongs to are visible in the iTunes iPod sync window, neither is Santana the artist.

This seems more like a snapshot of some previous sync selection persists within iTunes. I have reset the iPod to factory settings in iTunes, and I have done the "simultaneously hold the scroll wheel + menu button" reset on the iPod. So the device has been wiped, but iTunes keeps offering that same selection when choosing the "sync only selected playlists" option. Should I delete iTunes altogether from my Mac and restore it again from the cloud?

Apple Music track:

CD rip (iTunes Match):

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Answer 2

turingtest2

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Sep 9, 2017 10:35 AM in response to tuomofromfinland

iTunes cannot sync content that is currently in iCloud to the classic. You have to download it to the computer first. You can download from the cloud symbol that will show against the track or album. Or you can select a range and use the context menu.

tt2

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Answer 3

turingtest2

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272,943 points

Sep 9, 2017 9:26 AM in response to tuomofromfinland

Perhaps the way the playlists have been restored flags them as Apple Music content. I take it there is no local backup of your old library in Time Machine or similar? Have you checked the kind of the restored content to make sure that it isn't protected media?

I've assumed from the first image that the device has actually been wiped, but perhaps that is a preview of what would happen if you synced it. If the content is still on the device, and it turns out you need it, see Recover media from an iPod.

tt2

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Answer 4

turingtest2

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272,943 points

Sep 9, 2017 4:46 AM in response to tuomofromfinland

Each iTunes library contains a hidden ID. From the sound of things the way that you have restored the library means it likely has the same content, but has a different ID. You seem to have plenty of playlists but you could have possibly lost ratings and play counts. If iTunes transferred purchases from the device then you might also have created some duplicates in the library.

The first screenshot suggests that nothing is now selected to sync to the device. You can either sync all music, or sync a selection of playlists and/or genres, artists, and albums. I'd generally work with playlists only. Once you have made the selections you can sync to put the content back on the device.

tt2

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Answer 5

Sep 9, 2017 5:09 AM in response to turingtest2

Thanks for your reply! Yes, I am able to sync the limited number of playlists that are visible in the iPod sync window, but how to make the rest of the playlists visible in the iPod sync window? You mentioned iTunes library ID. Is it possible my iPod is somehow linked to the previous iTunes library ID? If so, is there a way reset the iPod to connect to the current iTunes library ID?

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Answer 6

turingtest2

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Sep 9, 2017 5:54 AM in response to tuomofromfinland

Do you subscribe to either iTunes Match or Apple Music, or was some other kind of cloud backup involved? Apple Music content cannot be used with an iPod classic, and you can only transfer content that is downloaded to the computer rather than shown in the cloud.

tt2

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Answer 7

Sep 9, 2017 8:30 AM in response to turingtest2

Yes, I subscribe to both iTunes Match and Apple Music. My CD rips were successfully restored from iCloud (iTunes Match), and they are organized in some 60 playlists in my iTunes library. However, the iPod sync window shows only maybe a fifth of those. And yes, I know a MacOS or iOS device is required for the Apple Music content, so I'm not expecting them to be available to sync to an iPod.

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Answer 8

Sep 9, 2017 10:35 AM in response to turingtest2

You are so right. The playlists, artists and albums become visible in the iTunes iPod sync window after I download them to the Mac. A huge thank you! You saved my weekend!

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Answer 9

turingtest2

Level 10

272,943 points

Sep 9, 2017 12:21 PM in response to tuomofromfinland

You're welcome. 🙂

tt2

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