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.

> their new computer. The computer had no songs on it and the Zune synced with that machine and wiped all the existing music

This is identical to the default way the iPod worked. If you bought a new Mac, and needed to get your music onto it, you had to use the migration assistant (connect via ethernet or firewire) or copy the music yourself. If you just plugged in your iPod to the new 'empty' mac and hit Sync, you'd lose your music too.

This was done as a show of good faith to the RIAA - their nightmare was that users would go from one dorm room to the next, dumping all their music onto all their friends' PCs. As a result, an iPod (or indeed still an iPhone today) can only sync with one music library (aka one computer) at a time. If you put it in "manually manage" mode, you can copy onto the iPod/iPhone from a 'foreign' library, but you can still never copy in the other direction. And all of this is true even when your music has no DRM encryption.

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

I thought to myself: "I better add these two new albums to my ipod so that I can listen to them while away". I plug in the ipod, itunes loads up, I walk away. I come back 10 minutes later and it had not finished yet and I wonder what is going on. Turns out it deleted my entire 40gb library off my ipod and started re-syncing. I had to leave so I unplugged the ipod but it was basically useless at that point.

I do agree with Microsoft in general but Apple seems to be very much the same in my experience.

Some time later, I connected it to my dad's computer to put a couple more songs on it. The first thing it did when I hit "sync" was delete everything on the iPod.

I learned that day that "sync" meant something different to Apple than it did to me.

I'm sure it gave me some kind of prompt but it was not a clear "hey this is going to delete everything" prompt.

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.

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.