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iTunes Makes Me Afraid

I’m completely syncing my iPhone to my ThinkPad for the first time in a long while, in preparation for installing iOS 4, and keep running into software behaviors that are the antithesis of good product design.

iTunes keeps breaking one of the cardinal rules of design—it keeps me in a constant state of suspense, worried that it might permanently delete songs, contacts, and lots of app$ in the process of trying to figure out how to properly back it up.

The first problem was this dialog box, which warned me that purchased items would be lost when I synced unless they were transferred to the iTunes library. But nowhere did it instruct me how to transfer them to the library. It took me 3–5 minutes to determine this after I hit cancel. The proper behavior would have been for the dialog to offer to start the process for me, or at least throw up an image that showed me exactly what menu item to click on.

The next problem was that I was primarily thinking of the measly 4 songs I have on my iPhone. BFD if I lose $4 worth of tunes. But no, it really meant all purchased items, including countless apps I had spent much time and dollar$ collecting and customizing, and I only realized how much I might have lost when the syncing of those 4 songs seemed like it was taking far longer than necessary.

And that led to the next fear—iTunes was in a strange state that had Apps not synced, but somehow backed up from my iPhone anyway. And when I selected the check box to sync them, iTunes warned me that this would overwrite all apps and application data on my iPhone. But I want to backup the applications and data, so these messages implied that I might have to choose between the two. This is a horrible feeling, directly caused by Apple’s software engineers!

I’m clearly not the only one who has had a similar fear. Read this how-to on the apple blog, and then read all of the comments below, from all the other fearful users.

And this article makes me doubt that I can sync the applications without losing data, although I’m not entirely sure, since I don’t plan on deleting the apps before syncing, but rather letting iTunes do so.

Posted in Design, Usability.


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