iPhone & iTunes sync - Don't want

Updated: January 8, 2016

The singular great advantage of having a dedicated test machine is that you can afford to load it with potentially unwanted software without having to worry about changing or damaging your production setup. In my case, the Lenovo G50 laptop with its Windows 10 installation, among many other Linux distros residing on the disk, is the perfect test bed to try iTunes.

Why? Well, I have an iPhone 6. I got it as a gift, ergo free, and for the past 7-8 months, I've been testing and trialling it, conducting technology experiments as much as deep anthropological study into the human psyche and glamor affection. So far, I found it very much not to my liking. It's a great opportunistic camera, the hardware is great, but the day-to-day use is average. One aspect of vicious struggle is music, as I have briefly illustrated in my Rhythmbox article recently. Therefore, I decided to bite the bullet and try iTunes, to see if this software really makes that much of a difference when working with an Apple product. Follow me.


The iTunes adventure

Installed, no problems. Launched the program. Well, I have to admit the interface is not very intuitive. In fact, I had to search for help both inside the application as well as online to try to figure out how to sync music onto the iPhone.

The first bit of trouble was with the authorization of the computer. This is a necessary step, and you can authorize up to five devices for use with iTunes and your Apple account. I'm not sure why there's a restriction, but it sure pleases me not. On top of that, you have to trust the computer on the iPhone itself, before its contents will be mounted and presented inside iTunes.

iPhone connected, now what

Authorize computer

Authorized, 1 out of 5 computers

For the purpose of the authorization, you will need to sign in with your Apple account. Then, separately sign into iTunes. Two different logins, which isn't bad from the security perspective, but a little cumbersome. However, regardless, I was still clueless about how to sync music onto the phone.

Reading the manual, something I've not done in probably a decade, I was supposed to see some kind of a sidebar for the connected phone, and then, the option to sync files would be there. Except I had no such option with my iPhone and the particular iTunes setup.

Help is of no use

No sidebar, no sync

No sync, no love

Bob Marley sang thusly. Well, I wasn't sure why I had the problem, so I decided to search some more. This mean clicking every possible little thing, exposing the file menu, and then diligently searching through every single option and sub-option. Eventually I managed to locate the Sync button, but it was grayed out.

Sync grayed out

Well, more online searches. Most of the people in the forums, apart from being haughty and mighty, were recommending the distraught users to reset their phones. Well, that sure helps. It's like reformatting and reinstalling your Windows when an application hiccups.

I tried something simpler. Closing the program, disconnecting the iPhone and trying again. Then I got a weird little prompt from the software telling me it could not read the contents of my phone, and that I should reset the device. My problem escalated from trying to use a program to copy a bunch of songs onto a smartphone to a full-blown nuclear war. Not what I had in mind. Naturally, I uninstalled iTunes and sat down to write this article.

Cannot read contents


So I'm wondering why iTunes decided to suck. I have two possible theories. One, I used the iPhone for my Linux testing quite a lot, and probably connected it to two dozen distros over the past several months. Each time, iPhone would ask me if I trusted this and that computer, so I may have exhausted the five device limit somewhere internally, which is why it will not let me sync the files.

The other options is that Rhythmbox somehow corrupted the phone. But then, if all it takes to destroy a device and its sync-ability is one innocent little sync, then it is badly designed. Instead, using MTP and plain folders would have worked just as well, and with infinitely more robustness. I don't know if this is true, it's just a hypothesis, but if so, the fail magnitude is just as big.

The third option is that something is just broken in the iPhone-iTunes interface. Sure, it works for millions, but that does not matter, because it does not work for me. Trying to blame other pieces in the stack is fine, but in the end, however you stack and combines the pieces and odds, the phone failed to give me what I need.

One last thing

If when reading this article you're thinking iTunes Match, Spotify or any other solution which works for you, please electrocute yourself. This isn't about your style and how you live, and how much money you have to spend. I've got Amazon Prime, I've got all the free music and storage I need. That's not the point. The point is, I want to copy files and/or sync files from a computer to a smartphone. That's all. The fact you can do it a hundred different ways is irrelevant. If other devices and operating systems can achieve the same result, I see no technological reason why an Apple phone shouldn't.


It's been many months since I got this shiny plastic brick, and I still haven't managed to successfully copy and play a single music file. At the same time, various Android phones, Windows Phones and the one Ubuntu Phone I own all manage this task with utter ease. This tells you all you need to know about how Apple approaches its products and users, and what kind of regime you need to follow to attain Nirvana.

Aesthetics and hardware aside, iPhone 6 does not have a single usability advantage over its rivals. None whatsoever. Moreover, the ultra-restrictive way you must do things is frustrating and maddening and utterly sub-100 IQ. Fine for people who believe California is the center of the Universe, less so for people who can spell cynicism without getting confused. I will not partake in this silliness. Which means the moment my bunch of Apple stocks finally makes some kind of a profit, I will most likely dump them all back into the shares sea. There is no reason to keep investing in this. All I wanted was to play an MP3 file. That's all I asked. Won't let me play? Won't give you my money. Fair deal. And you're welcome, dear readers. I'm suffering so you don't have to. We're done.