Big Sur, Music and iPod Shuffles

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.

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.