Tonight I've been messing around with this new open-source cross-platform rebuild of the Zune app, and it's working great on my MacBook! It's got built-in encoding to WMA Lossless (a format literally nobody but Zune freaks care about) and it's tackled my FLAC and ALAC files with no complaints.

#zune

https://github.com/magicisinthehole/xune-releases

GitHub - magicisinthehole/xune-releases: Xune — Release builds for testers

Xune — Release builds for testers. Contribute to magicisinthehole/xune-releases development by creating an account on GitHub.

GitHub
I've noticed in the Zune subreddit that there are, like, *a lot* of people who were all-in on the Zune back in the day but have since moved to Linux or Mac, but the desktop client doesn't run well in Wine or a VM. I've been running a Windows 10 install on a backwater partition of my home media server just to sync music to my beloved Zune HD. Being able to buy an album off Bandcamp, download it to my laptop, and then pop it onto my Zune without having to deal with booting to that Windows install and moving the files over is huge for me.

@trixter wait, it doesn't work on VMs?? Like, if you spin up an XP instance on a VM, the zune software won't work right? That is wild.
Kudos to Microsoft for not just figuring out how to make the user experience worse back in the day, but having the foresight to ensure people in the future can't have good things either.

('Kudos', is of course given with much sarcasm. Many air quotes. Lots of the above text is to be read in Daria Morgendorfer's voice)

@GabeReal The app technically works, but it doesn’t like recognizing the device via USB.
@trixter Oh yeah, I can see that. I have to go out of my way to get storage data into a VM.
I usually have to take whatever data I am trying to move into the VM and turn it into an ISO file and then put it into a datastore and then have the VM mount the ISO as if it were a disc.
And I don't think that route would work for a portable music player.... :/