Big Sur, Music and iPod Shuffles

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Level 1

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Big Sur, Music and iPod Shuffles

I have a collection of the 2nd gen iPod shuffles that I used to use quite regularly but had been put aside and forgotten about until a couple of weeks ago. Thought I'd get them out again and put them to use, but I am having some real issues trying to work out how to get them to work under the Big Sur / Apple Music world.

The shuffles were all previously used with my Macbook Pro on older versions of OSX with iTunes, and they worked fine. The physical music files are stored on a NAS on my network, with just the iTunes library information held on the Macbook Pro itself. I don't subscribe to Apple Music and have no interest in doing so, just want to sync my own files.

I have read lots of information online from various sources about Shuffles and Big Sur, ranging from "they're not supported" to "you do it in Finder now", to this support article that sounded very similar to my issues, but didn't seem to get resolved. It seems that there is little genuine info about using Shuffles and Big Sur, most of the articles and screenshots all mention them but are actually based on an iPhone, which looks and behaves very differently.

The main problems I seem to have are:

When I plug in my Shuffle, it shows up in the Finder sidebar, and I can manage the device's sync settings from there, but I cannot do anything else. There is no way that I can see to perform some sort of manual drag & drop of music onto the device. This is all I see:

If I try to manually drag & drop music from my library within Apple Music onto the Shuffle, it says "syncing", and in Finder the a similar thing shows up, but with some Shuffles the sync doesn't finish, or with others it finished but there is still no music shown on the device within Apple Music, although Finder would indicate that some storage space has been used

So is this a lost cause? Am I never going to be able to successfully manage these little iPods via the "new world" of Big Sur / Apple Music? Do I actually have to (gasp!) go back to using iTunes on a Windows laptop to keep using them? It would be a shocking indictment of Apple if the only way to use their own hardware was via another company's OS!

Posted on Oct 5, 2021 3:40 AM

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Answer 1

Top-ranking reply

Frank F.

Level 2

234 points

Nov 18, 2021 3:06 AM in response to bigjules

I experienced the same problem after I updated my MacBook to macOS Big Sur from an older version which still had iTunes, and spent some time examining the problem and possible workarounds.

In short: Loading tracks on and (indirectly) removing tracks from the 2nd-generation iPod shuffle is still possible with macOS Big Sur and the Music app, but displaying the tracks stored on the device and managing (or at least preserving) their play order no longer works.

In the Music app on your Mac, create a playlist which you name "iPod shuffle" or whatever you call your device. Maintain this playlist by adding any new songs you want to hear and removing all songs you don't want anymore. Take care that the total size of the playlist does not exceed the capacity of your iPod shuffle (minus the amount reserved for disk use, if any).

To update your device, connect it to your Mac and select it in the side bar of the Music app. At the bottom of the window, next to "Autofill From:" select the playlist you created for your device. Under "Settings...", check the "Replace all items when Autofilling" option and click "OK". Finally, click "Autofill". The Music app will now remove all files from the iPod which are not in that playlist, and then transfer the new ones. If you replaced a lot of songs, you will see the "Available" capacity jump up at the start and then slowly decrease again.

After this operation completed, eject your iPod from the side bar of a Finder window (not the Music app), then disconnect it and enjoy the new music on it.

Unfortunately, however, there is a big drawback. While the audio files themselves are transferred successfully, their playing order is not. If, true to its name, you always use your iPod shuffle in shuffle mode, you won't bother or even notice it, but if you use linear playback mode, the iPod will play all the tracks in alphabetical order of their titles (and optional "sort as" fields), ignoring the album and track number information, which pretty much renders this mode useless.

If anyone found a solution or workaround for this (other than resorting to iTunes on another Mac or PC), I'd be most interested to learn about it.

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Answer 2

bigjules Author

Level 1

10 points

Nov 20, 2021 2:15 AM in response to Frank F.

Thanks Frank F, that's really useful to know. The issue with the play order doesn't really worry me - as you mentioned, I use it in its original intended "shuffle" mode anyway.

It's a big shame on Apple that they treat owners of older (but still perfectly functional) products so badly. The excuse "time marches on" doesn't wash any more, not in this day and age with more and more focus on environmental concerns, i.e. re-using / recycling / repairing kit and extending its life. I love my shuffles, as I'm sure you and thousands more do too - this lack of proper support leaves us as second-class citizens in the Apple ecosystem.

I'll give your suggestion a go and see how it works out. However I confess it does sound like a lot of "faff" to get the right results, and using iTunes on my Windows laptop might actually be the better long-term option, I think. Thanks so much for taking the time to reply though :-)

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Answer 3

Frank F.

Level 2

234 points

Nov 23, 2021 7:10 AM in response to bigjules

The method I described does not add any effort in my opinion. I actually think it's pretty convenient to prepare what I want to have on the iPod shuffle "offline" in advance on the Mac by maintaining the dedicated playlist. Selecting that playlist for autofill and enabling the option to replace files (to not just transfer songs added to the playlist, but also delete ones removed from it) only needs to be done once. Whenever the device is connected, updating its contents is an automatic process started with a single mouse click on the "Autofill" button. As a matter of fact, I have been using this method all these years when iTunes was still around.

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Big Sur, Music and iPod Shuffles

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