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iTunes: another tale of woe in UX

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I know that pointing out errors in iTunes is a bit passé but Apple keeps releasing new versions of this thing without addressing the fundamental problems that it has as a synchronization client. The software has to synchronize with hardware from only one manufacturer---the same one that makes iTunes. I'll leave off complaints about the horrific, very old and utterly non-scaling UI and just regale you with a tale of a recent interaction in which I restored my phone from a backup. In that sense, it's a "user experience". In this tale, we will see that two of the main features of the synchronization part of the iTunes software---<b>backup</b> and <b>sync</b>---seem to be utterly misinterpreted. Spoiler alert: it all works out in the end, but it's mind-boggling that this is the state of Apple's main software after almost 15 years.<fn> 10 million new iPhones were sold over the weekend. Their owners will all have the pleasure of working with this software. <h>Restore from backup</h> <b>Me:</b> *attaches phone* <b>iTunes:</b> Restore from backup? <b>Me:</b> Sure! <b>iTunes:</b> *shows almost full iPhone* There you go! <b>Me:</b> Thanks! That was fast! <b>Me:</b> Wait...my phone is empty (no apps, no music, no contacts) <b>iTunes:</b> *blushes* Yeah, about that... <b>Me:</b> *reconnects phone* <b>iTunes:</b> *shows nearly empty iPhone* What's the problem? <b>Me:</b> Seriously, RESTORE FROM BACKUP (select EXACT SAME backup as before) <b>iTunes:</b> On it! Sir, yes sir! <b>Me:</b> OK. Apps are back; contacts are back. No music, iTunes? What part of the word "backup" is causing difficulties here? <b>iTunes:</b> *blushes* (again) Ummm, dunno what happened there <b>Me:</b> Fine. It was randomly selected anyway. <b>Me:</b> Select random music from this playlist <b>iTunes:</b> Here ya go! <b>Me:</b> Sync <b>iTunes:</b> Nothing to do <b>Me:</b> Sync <b>iTunes:</b> Seriously, dude, there's nothing to do <b>Me:</b> SYNC <b>iTunes:</b> Done <b>Me:</b> No music on phone. Do you understand the word "sync" differently as well? You know, like how you have trouble with the word "backup"? <b>iTunes:</b> ... <b>Me:</b> *notices that size of playlist exceeds capacity of iPhone* <b>Me:</b> that's 17GB of music. For a 16GB iPhone. <b>iTunes:</b> Yep! Awesome, right? <b>Me:</b> Is that why you won't sync? <b>iTunes:</b> Error messages are gauche. I don't use them. Everything is intuitive. <b>Me:</b> Fine. Reserve space when selecting music: 1GB (don't need more extra space than that) <b>iTunes:</b> NP! Here's 15GB of music. <b>Me:</b> Wait, what? You're supposed to leave 1GB empty *of the available space* not the *total size of the device* <b>iTunes:</b> Math is hard. ... You do it. <b>Me:</b> Fine. Reserve 4.2GB? <b>iTunes:</b> Done. <b>Me:</b> Now I have a 28GB playlist. <b>iTunes:</b> *pats self on back* <b>Me:</b> Reserve 3.2GB ... and "delete all existing" and "replace"? Now does it work? <b>iTunes:</b> 9GB for you <b>Me:</b> *tweaks settings 2 or 3 more times* <b>iTunes:</b> 10.5GB <b>Me:</b> Perfect. That was totally easy. <b>Me:</b> Sync <b>iTunes:</b> On it! *hums to self* <b>Me:</b> Why are you only syncing 850 songs when the playlist has 1700 of them? <b>iTunes:</b> *continues humming* <b>Me:</b> Fine. *wanders away* <b>iTunes:</b> Done <b>Me:</b> Sync <b>iTunes:</b> *syncing 250 more songs* <b>Me:</b> What the hell? <b>iTunes:</b> Done. <b>Me:</b> Sync <b>iTunes:</b> *syncs remaining songs* <b>Me:</b> This is ridiculous <b>iTunes:</b> Done <hr> <ft>It has been pointed out to me that I am using this software in a somewhat archaic way: to wit, I am not allowing iTunes to synchronize all of my data to the cloud first. Had I done that, it is claimed, I would have had fewer problems. I am, however, skeptical. I think that a company that can't even get local sync working properly after 15 years has no business getting any of my data.</ft>