Sync new purchases to iPod Classic

I recently refurbished an old iPod Classic, and purchased some albums in the iTunes Store (yes, it still exists!) with the idea of trying what counts as oldschool in the 21st century – listening to music on something that doesn't also receive email.

Once I found out that most iPod Classics are capable of playing Apple's lossless format, ALAC, I really wanted to sync them over to experience this heretofore unimaginable audio clarity.

However, even though I could download them, the albums refused to show up in the sync list. Switching back to AAC worked fine, but ALAC was not working.

Turns out iTunes itself does not provide lossless downloads.

Because I also have an Apple Music subscription, the lossless versions of my albums were being downloaded, but in the protected .movpkg encrypted format that only works with Apple Music.

So the only way you can sync all your iTunes purchases is setting 256kbps AAC:

Another hiccup is that Apple recently removed some iPod sync support from MacOS Sequoia (15.4.1).

This isn't a showstopper for me as I have Macs of various vintages running everything from OS9 to Ventura, but it's an annoying thing for Apple to do right as iPods are having something of a renaissance.

There is a reported workaround that seems to work for some, if you happen to run into this.

As an addendum, here's a photo of my 4th gen classic, refurbished with a new battery from AliExpress, and the iFlash ATA1 microSD adapter.

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