iTunes: another tale of woe in UX

9/24/2014 - Marco (updated on 11/13/2017)

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 -- backup and sync -- 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.1

10 million new iPhones were sold over the weekend. Their owners will all have the pleasure of working with this software.

Restore from backup

Me: attaches phone iTunes: Restore from backup? Me: Sure! iTunes: shows almost full iPhone There you go! Me: Thanks! That was fast! Me: phone is empty (no apps, no music, no contacts) iTunes: blushes Yeah, about that... Me: reconnects phone iTunes: shows nearly empty iPhone What's the problem? Me: Seriously, RESTORE FROM BACKUP (select EXACT SAME backup as before) iTunes: On it! Sir, yes sir! Me: OK. Apps are back; contacts are back. No music, iTunes? What part of the word "backup" is causing difficulties here? iTunes: blushes (again) Ummm, dunno what happened there Me: Fine. It was randomly selected anyway. Me: Select random music from this playlist iTunes: Here ya go! Me: Sync iTunes: Nothing to do Me: Sync iTunes: Seriously, dude, there's nothing to do Me: SYNC iTunes: Done Me: No music on phone. Do you understand the word "sync" differently as well? You know, like how you have trouble with the word "backup"? iTunes: ... Me: notices that size of playlist exceeds capacity of iPhone Me: that's 17GB of music. For a 16GB iPhone. iTunes: Yep! Awesome, right? Me: Is that why you won't sync? iTunes: Error messages are gauche. I don't use them. Everything is intuitive. Me: Fine. Reserve space when selecting music: 1GB (don't need more extra space than that) iTunes: NP! Here's 15GB of music. Me: Wait, what? You're supposed to leave 1GB empty of the available space not the total size of the device iTunes: Math is hard. ... You do it. Me: Fine. Reserve 4.2GB? iTunes: Done. Me: Now I have a 28GB playlist. iTunes: pats self on back Me: Reserve 3.2GB ... and "delete all existing" and "replace"? Now does it work? iTunes: 9GB for you Me: tweaks settings 2 or 3 more times iTunes: 10.5GB Me: Perfect. That was totally easy. Me: Sync iTunes: On it! hums to self Me: Why are you only syncing 850 songs when the playlist has 1700 of them? iTunes: continues humming Me: Fine. wanders away iTunes: Done Me: Sync iTunes: syncing 250 more songs Me: What the hell? iTunes: Done. Me: Sync iTunes: syncs remaining songs Me: This is ridiculous iTunes: Done

  1. 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.


NIce reading!

I'm with you that iTunes needs a serious re-write (I guess refactoring won't get to the best end). If they rewrite that thing once a day I hope the to the software-architecture right and split "media player / media libraries" from "synchronization tool". For the later I like to have this as part of the operating-system so other Mac Apps and devices can easily use it too. Even Microsoft got this part right (after some tries).

Just two thoughts about your iTunes experience:

Maybe many of the 10 Mio's don't need to sync their new iPhone that way. At least I will not need it. Most of the data is in the Cloud anyway (Google Calendar, Google Contacts, Apple Contacts, Apple Calendar, Dropbox, Google Drive, iDrive, Spotify, iCloud for apps-data, Photo-Streams, etc.). For me this even includes all my music with is in iTunes Match (and a backup on my local server). Means one does not need to sync them but just stream them as need or click the download button for the selected songs, albums, interpreters, playlists, etc. to have them offline.

The other interesting thing is that I had syncing issues with iPhone(s) and iPad(s) since using them (time back when I sync't them anyway). Interestingly I never ever had or have sync-issues with my "iPod Classic". Ok to be fair there is no need to music-selection but syncing the whole music library. Maybe that the safer here. Hmmm...

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