I recall reading this story of some user doing a sync with Zune on their new computer. The computer had no songs on it and the Zune synced with that machine and wiped all the existing music off his Zune without warning him(or something like that its been years). I recall thinking, yep thats Microsoft. And to this day I still encounter dumb ways of thinking in many of their products. The endless negative stories I hear about Windows 11 are just the tip of the iceberg. The entire company has to be following a cohesive vision with leadership at top needing to be truly involved to make great end to end products and really Microsoft has not been that in a long time.

I was a zune user. I had my music organised meticulously and could simply drag and drop to my zune from my (parents) windows desktop. It was simple and it was fantastic.

Then I got a iPod so I needed to download iTunes. I downloaded iTunes, it told me to import my music. I imported my meticulously organised collection. It duplicated every single file into the iTunes approved format (AAC?) - my meticulous collection was now less meticulous, messy even.

It caused me to swear off Apple products for decades. Though it also led me to some very basic programming in order to delete the duplicates. I was only partially successful.

Programming led me to use Linux, before I eventually moved over to Mac. I like to think this was their plan all along.

I remember Microsoft introduced a DRM / certification program they called "Playsforsure".

Two years later they introduce the Zune, which could not play "Playsforsure" music people had purchased from MSN..

to be honest, apple did this when it launched apple music.

It did all kinds of things like hiding your music library, merging your music with apple's music, all kinds of nonsense.

You used to be able to put your music on your phone easily, then it became sort of a gauntlet in favor of apple's subscription service.

To be fair, iTunes suffered from the same defect at one point. Microsoft is now a clinic on defective design, execution, and attitude. But back then it wasn't that bad.

The iTunes case was also a classis UI 101 blunder combined with stupidity. If there was no iPod plugged in, the "Sync on connection" toggle in iTunes simply disappeared. First of all, when something is inapplicable, you grey it out. You don't just make it disappear.

But in this case, even greying it out would have committed the same blunder, because the default state for this behavior was YES.

So if the hard drive in your computer went bad and you installed the OS fresh on a new one, thinking that all your music was backed up on your iPod, you were right... until you plugged it in.

So, so dumb.

And finally: Apple never addressed the lack of "computer overwrites mobile" and "mobile overwrites computer," which Palm OS syncing nailed in the '90s.