Apple's iTunes purgatory for Windows: There has to be a better way

Apple's iTunes purgatory for Windows: There has to be a better way

Summary: The Apple iOS platform is a thing of beauty, but for Windows users, iTunes is pure and utter hell.


The Apple iOS platform is a thing of beauty, but for Windows users, iTunes is pure and utter hell.

Anyone who has read my material long enough knows that I've historically been pretty critical of Apple, and I've given the company a ton of flak in this column. And it's been for reasons which I think they deserve.

I've talked about how I probably (and this too may change depending on my needs) will never own a Macintosh computer and why the behavior of their hardcore fan-base makes me ill.

I've also criticized their utterly inconsistent app approval policies and the bizarre isolationist ideology that the company has now embraced.

All of these things I know to a large extent will not only be ignored by the company, but I know that Apple is a Snow Leopard that is unlikely to change its spots anytime soon, this despite my appeals towards a more sane relationship with the company for its customers, content providers and developers.

I'm sure that I'll continue to fight the good fight and hammer away at them for these reasons stated above, but I've come to the realization that it probably makes sense to criticize aspects of the company and its products which can be improved and/or changed, and on issues where the company might actually be receptive.

That being said, since I've owned my iPad, the device has been pure joy. I love the elegance of its design, the functionality, the responsiveness of the user interface, and the ease in which I am able to interact with it and how it makes me more productive.

I have zero complaints about the device itself. Sure, there are certain feature improvements I would like to see in future iterations of the iOS and in the iPad hardware, but generally speaking I am a very satisfied iPad customer. I think Apple did a fantastic job with the first version of the device and for that, they should be commended.

Unfortunately, the iPad and all iOS devices have an Achilles heel. And that fundamental weakness is iTunes.

Now, I can't speak for iTunes on the Mac platform. I don't own a Mac and I don't use one regularly enough to know how it performs and how stable it is. But speaking purely from the Windows perspective, iTunes is an absolute stinking piece of crap. It's slow, it's buggy, it's unstable, and thoroughly unpleasant to use. To quote one of my colleagues in the biz, it sucks dead gophers out rusty tailpipes.

Since the day I got my iPad, I have avoided using iTunes for any reasons whatsoever. I don't listen to MP3s or AACs from iTunes or download music to it, I only use streamed content, so I have very little reason to sync to a PC. My movies stream from Netflix or I download them directly to the iPad wirelessly from the device's own built-in iTunes.

To upload content to the device I use any number of iOS apps that allow me to pull data from various cloud storage services, such as DropBox or Google Apps. I can even transfer data directly to the iPad wirelessly using apps like Goodreader or pull from content repositories of my own making, like OPDS feeds for Stanza.

In fact, the only time I've been forced into using iTunes is when I had to activate the device for the first time, and when I had to sync EPUB content to iBooks before an iPad-optimized Stanza came out, which has any number of ways to retrieve the books, including email attachments.

So when Apple announced the iOS 3.2.2 update which patches the PDF rootkit and web-based jailbreak vulnerability, I knew I was in for an unpleasant experience.

Now, Apple had released an interim patch, 3.2.1, that fixed some issues related to wireless networking which I never really encountered on my home 802.11n WLAN, so I gleefully skipped that one. In fact, I was hoping I could completely avoid any iTunes-related patching activity until iOS 4 for iPad came out, sometime in the fall.

But given the severity of the Jailbreakme vulnerability, and how many PDFs and websites I look at with my iPad, I knew that I had to deal with it immediately. It was unavoidable.

So around 11PM Wednesday night, I upgraded my iTunes on my lone Windows 7 physical system in my wife's office and hooked up my iPad. I immediately saw the patching message requesting an upgrade of the iPad system software.

I saw the backup procedure start, and I walked away, figuring the whole thing would be done in say, an hour. If that. I had a lot of apps installed, about eight screens worth, but only about 4GB of data on it. Couldn't take that long, right?

I went upstairs to the living room, watched Morgan Freeman talk about the secrets of the universe for about an hour and a half, and saw that the backup appeared to be about 1 percent done. Yikes. So I retired for the evening, expecting that when I woke up to make my morning coffee, my iPad would be ready to go.

Well, it wasn't. It was about 25 percent through the backup, nine hours later. WTF? No status messages indicating where it was stuck, or what other activity was going on in the background. Just a green bar about one quarter complete.

Well naturally I assumed there was an issue with the PC. I saw it wasn't charging the iPad and that it was almost out of juice, and perhaps the ports weren't negotiating at full speed. So I researched the web a bit and found out that Asus offers a free utility that can fix the low power USB issue to allow the iPad to charge on various types of mainboard chipsets. I installed that, and the iPad indeed began to charge, but it didn't help with the backup speed. It still looked like it would take forever.

So after an hour or two of troubleshooting and trying various other things such as resetting the device, iTunes and the iPad backup was still like watching paint dry.

From what I've read on various fora and Apple-related websites, if your iOS device is taking eons to backup, you probably got an app or a file that's misbehaving and it's messing up the backup process. So the first thing you want to do is remove all your pictures and music and videos that could be a potential problem.

If you still can't perform a backup, the only sure fire way to fix that is to factory reset the device and wipe the memory.

I could do that, but I really, really didn't want to. I had a bunch of settings and home screen icons for web pages and all kinds of customizations I didn't want to lose. And sure, I could re-download the apps I paid for without having to buy them again, since I had all the email receipts from the App Store, and iTunes can retrieve the purchase logs for you to view, but there's no easy way to keep track of your downloads on the device itself.

This is in contrast with Android's Market app, which has a dedicated Downloads screen for showing you all the apps you've bought and installed. And unlike Android, the App Store doesn't sync your settings, preferences, stateful app data (high scores, levels achieved in games, etc) and home screen bookmarks to the Cloud, as Android and Google can.

On Android, if I decide for any reason to do a complete wipe of my phone, or if my phone dies and Verizon has to give me a replacement Droid, all I have to do is log in with my Google account on initial setup and the Android Marketplace has a "Downloads" screen with all of the apps that were previously installed on the device, which I can choose to re-install one at a time with Android 2.1, or restore all of them in one fell swoop with Android 2.2.

I can also set the Droid to automate updates so when a patch to an app is released, the device downloads it automatically. You can't do any of this on iOS or with the App Store.

And unlike my Droid, the iPad also doesn't have a Micro-SD slot to maintain other settings and data that your apps can access when they've been restored.

In other words, if you are unable to perform a backup to iTunes, and you set your iPad back to factory, you are back to square one. You are hosed.

So at 5PM, I put my tail between my legs and schlepped over to the Apple Store in Garden State Plaza, hoping that the Geniuses had some special forensic tools or advanced diagnostic capability that would permit them to back up the device on a Mac, install the update and restore my apps and settings. I mean, this was the Apple Store, right? They could fix something as trivial as this, right?

So I sat in rush hour traffic on Route 4 and crept over to the Apple store in the mall. Naturally, the place was mobbed. Oy.

Apple Store in Paramus, New Jersey.

But there was a nice Apple employee there to greet me, who took my name down and made an appointment for the Genius Bar, which was fielding Mac and iOS customers in a coordinated and orderly fashion. Okay, so far, so good.

After about a 30 minute wait -- which was much better than what I expected, I placed my iPad in front of the Genius, and explained my problem, and asked him if he could perform the backup and upgrade.

"What iOS 3.2.2 upgrade?"

"Uh, the one that came out last night? The one that keeps your device from being compromised and jailbroken by infected PDFs or remote web exploit?"

"Umm, let me see... yeah we just need to download it on my MacBook here and we can try syncing it. But our bandwidth at this store is kinda sucky, it might take fifteen or twenty minutes for me to pull it down from the Internet."

"Wait, nobody has come in today asking to get their device updated?"

"I didn't even know about it until you told me! Thanks dude! Hey is that a OtterBox Defender case? I've never seen one of those yet. Awesome man!"

"Yeah, the lady up front that took my name down and the sales guys up front really dug it too. So do you have any diagnostics to figure out what app or whatever is messing up the sync?"

"No man, the only thing we have is the same iTunes a regular customer has, with clean Macs. At the store we really have no way of finding out what's messing up your iPad. The only thing that's different is that we can't save your data on our laptops. You know, for privacy reasons. I can try syncing your iPad to this Macbook, and maybe try to force the upgrade without a backup, but if it doesn't work, we'll have to factory reset the device. If you call Apple on the phone, they'll probably tell you the same thing."

"Alright man, I guess we'll try to sync it to the Mac and if it fails, we factory default it with the new software."

"No problem dude."

The Genius Bar at the Apple Store in Paramus, New Jersey.

I admit the Apple store people were really nice and pleasant to interact with. Unfortunately, after we pulled down the 3.2.2 software update, the MacBook couldn't back it up any faster, so we were forced to wipe the device clean. I lost everything.

If iTunes is just as much as a black box to an Apple Store employee, then what the hell did I need to go to the mall and waste two hours of my time for?

Apple, face it. iTunes is a piece of garbage. On both the Mac and on Windows. You need to figure out how to make iOS devices completely independent of this piece of junk if end-users are unconcerned with uploading music to iPods, iPhones and iPads. And I shouldn't require iTunes to activate my iOS device in the first place.

If Google can manage to sync apps and settings to the Cloud and restore them using the wireless network after a full system wipe, then so can you. If Google can figure out how to do over-the-air wireless network updates, then so can you. If Google can figure out how to give end-users firmware files for out-of-band manual OS updates via simple USB copy, then so can you.

And if you are going to provide an application like iTunes to your end-users and support staff, then you can at least give it event logging and more detailed diagnostics, right?

I mean, you are Apple, right?

Is it time for Apple to finally fix iTunes and make iOS devices self-hosting? Talk Back and Let Me Know.

Topics: Operating Systems, Apple, Hardware, Mobility, Software, Windows


Jason Perlow, Sr. Technology Editor at ZDNet, is a technologist with over two decades of experience integrating large heterogeneous multi-vendor computing environments in Fortune 500 companies. Jason is currently a Partner Technology Strategist with Microsoft Corp. His expressed views do not necessarily represent those of his employer.

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  • Ah, but it is easily solved

    Just put it in a VM and run in under Linux, right? Solves everything, even when someone cracks your facebook account.
    • LOL!

      @honeymonster - great stuff for people with a good memory of a certain past column!
    • Buy a Mac

      @honeymonster ... and move the hell out of New Jersey. There, I just solved all your problems.
      iTunes on the Mac works just fine, on all my Macs.
      • RE: Apple's iTunes purgatory for Windows: There has to be a better way

        @HollywoodDog ...yes, and everyone should get a new macbook to they can sync their iPod/Pad and stop complaining about a _real_ problem with crappy software that the manufacturer blatantly ignores. brilliant, just brilliant!
      • RE: Apple's iTunes purgatory for Windows: There has to be a better way

        @HollywoodDog: to the land of fruits and I have to buy a Mac for the software to work... Yeah that makes sense you should run for President...yeah that's it! Man I missed it all of the years cussing iTunes.
      • Fascinating.

        To have such an emotional attachment to a device that one has to fabricate lies in order to appease themselves.

        You humans would do much better were you to adopt a more logical, and less emotional lifestyle.
        Tim Cook
      • RE: Apple's iTunes purgatory for Windows: There has to be a better way

        @HollywoodDog So your saying we haft to cash out $699 or up for a computer to enjoy one peace of software? No.
      • RE: Apple's iTunes purgatory for Windows: There has to be a better way

        @HollywoodDog ... I have enjoyed my iPhone 3gs except for trying to get it to communicate with my Macbook Pro in anyway. I have lost hours of work and content trying to add a couple mp3s when Itunes decided to delete a variety of apps I had paid for in the syncing process.

        When I travel without my laptop adding files is impossible. I get more functionality out of a 1Gb memory stick for playing music in my car than I do for a 32gb Iphone 3gs.

        Itunes and the iphones inability to mimic a USB mass storage device is the source of the problem. The author of this blog was actually very diplomatic about the problems with itunes and syncing. Probably because he has tried to avoid the hassles of itunes except for security upgrades.
    • RE: Apple's iTunes purgatory for Windows: There has to be a better way

      "the behavior of their hardcore fan-base makes me ill."

      Got news for you. People on the Mac side feel the same way about the hard-core Windoze supporters/Mac-haters.

      Can't we all just get along? ;-)
      Harvey Lubin
      • RE: Apple's iTunes purgatory for Windows: There has to be a better way

        @Harvey Lubin I can't speak for other windows users, but I personally am tough on Macs, simply because the user base bashed Windows OS's for at least a decade and now when there are security issues with Mac os (ones that are very similar to what they chastised MS about 5-10 years ago), it's suddenly not a real virus and it only happens to stupid users. Really? Then why all the hate all those years ago?

        With that said, I have no problem with people using Macs. I don't need one, and see no reason to pay a premium to switch (esp since i prefer desktop computers), but if you're considering a $1500+ laptop, you should at least consider a mac.
      • RE: Apple's iTunes purgatory for Windows: There has to be a better way

        @notsofast your right, the "I'm better than you...because we just work" crowd is now feeling the pinch and reality of a larger and non "knee pad" crowd that will jump off bridges if the goof ball Jobs told them too. No longer the sanctity of the Labyrinth...
      • RE: Apple's iTunes purgatory for Windows: There has to be a better way


        Not so fast.
        If you are going to be harsh on a user base for bashing Windows, you might want to look a little closer to home! First, the biggest Windows bashers I know are Windows users. Most mac users couldn't care less.
        Second, there are legitimate reasons to bash MS, the company, including immoral and illegal business practices that were rightfully brought in front of the federal courts.
        Third, if something is not a virus, it is not a virus. Making the distinction is not pedantic.


        You are a hypocrite. Troll.
      • RE: Apple's iTunes purgatory for Windows: There has to be a better way

        @Harvey Lubin

        Odd. I was just going to say that reading his columns makes me ill. Jinx !
      • RE: Apple's iTunes purgatory for Windows: There has to be a better way

        @Harvey Lubin That would have been nice, say about 1995. You Apple fans have built up a solid ten years or more of arrogant and annoying behavior...that's why people seem to hate Macs. It's not the Macs, it's the blindly devoted apple fanboy religion that has brought this on. Remember all the forum questions where someone would post a question about an issue with their Windows machine? Remember all the "get a Mac" idiotic replies that constantly showed up? I happened to work in an office that was mostly Mac at that time, and knew from experience that what they were saying about their Macs never crashing etc. was complete BS, yet you could never even ask a question about Windows without one of these idiots spouting off their baloney.

        So you're reaping what was sowed for many years by arrogant starry-eyed and blinded Mac lovers who thought buying a certain computer made them something special. Best thing you could do is just shut up and let it die off, but people are getting back at you for all the years of annoyances and lies and attitudes, you (speaking in general of Mac/Apple zealots) earned it.
      • But DeusXMachina

        you continue to rehash a very old argumnet that carries little weight anymore as the deed was done, and punishment handled out.

        Should we continue to judge you on the mistakes or deeds of your past, or would you logiclly argue that you are no longer that person, and therfore should not be judged on the misdeeds of your past?

        Then logic would indicate that the argument of Microsoft's past is no longer relavent to the company as it is today, as it looks to be following the conditions placed on it.

        On the other hand, Apple and their users are the ones that are incresinglly coming under scrutiny, as their words and actions are heading in a less then desirable direction in terms of ethical developement.
        Tim Cook
      • Can't we all get along?

        @Harvey Lubin
        Well, apparently not. ;) But you're right - the rabid zealots of each camp make everyone "ill": whether Apple, Linux or Windows. Reminds me of a saying "They are right in what they assert, and wrong in what they deny".
      • RE: Apple's iTunes purgatory for Windows: There has to be a better way

        @Mr. Spock<br>Considering that there is ample evidence that the behaviour in question was not an isolated incident, your reply is highly illogical.<br>Not to mention the fact that you choose to respond to MY post on a totally irrelevant part of the thread. Highly illogical indeed.<br><br>P.S. Anyone who actually took any advanced courses in logic knows full well that if there actually were a race or species that insisted on only following the dictates of logic, that species would soon be extinct. Oh wait, that's kinda already happened in the reset Star Trek universe.
    • RE: Apple's iTunes purgatory for Windows: There has to be a better way


      Odd. I was going to suggest he make a Hackintosh VM just for iTunes.

      Assuming his PC can do EFI. Maybe VirtualBox would do.
    • RE: Apple's iTunes purgatory for Windows: There has to be a better way

      "Apple's iTunes purgatory for Windows: There has to be a better way"

      Amen brother!

      This is timely, a few nights ago iTunes cleared every mp3 off my iPhone..... iTunes is a stinking pile... I hate it.
  • So the fix in the end...

    wipe the drive clean, reinstall the OS, then reinstall all your apps. Hmm...

    Cue the double standards...