iTunes for Windows must be one of the buggiest, most poorly written applications out there. In terms of wasted months of your life it definitely ranks up there with Lotus Notes and Media Player 12. I don’t know how well iTunes works on a Mac (I like computer mice with twenty buttons, so I never was a big Mac fan), but I think I read somewhere that iTunes for Windows is the leading cause of suicides among iPhone owners. The logic behind iTunes’ workflow is simply incomprehensible. It seems like any button you click in iTunes either forces you to accept some end user agreement or threatens to delete all applications and music from your iPhone.

Clicking the checkbox for application sync displays this ominous warning. Apparently, attempting to sync up your apps with your PC via iTunes will inevitably delete every app from your iPhone. I guess the main question here is: why?

People carry a lot of important data on their smart phones and iPhone users are no exception. Generally, it is a good idea to backup the data on your phone once in a while. iPhone 3G and later models come with USB 2.0 sync port that supports around 40 MB/s effective bulk transfer rate. I have iPhone 3GS with 32GB storage (29.33GB effective capacity) running OS 3.1.3. According to iTunes’ sync interface, I am only using about 6.5GB of available space. At 40MB/s it should take me around three minutes to back up all the data on my phone to the PC. In reality, however, the backup process takes about nine hours. Call me crazy, but this looks like a substantial difference.

From numerous other iPhone backup horror stories I have read, my nine-hour backup is far from the record. iPhone users are reporting sync operations running for days! Obviously, if you cannot backup your phone at least overnight, you will just stop backing it up altogether. When your phone inevitably dies, you will lose many months-worth of important information: contacts, messages, photos, and application data. I had my iPhone for just over a year and I would rather lose my wallet with all my money, documents, and credit cards than lose the data on my cell phone.

So why exactly does it take so long to backup a few gig of data on your iPhone? The problem is with the iTunes application, which uses iPhone’s meager system resources – instead of the big CPU inside your computer – to handle various backup-related tasks such as indexing, compression, and verification. This is like unloading gravel from a dump truck by scooping it up with your bare hands and tossing it out two handfuls at a time.

Upgrading my iPhone 3GS to OS4 from start to finish took about 19 hours. Most of this time was spent by iTunes to back up 6.5 GB of data on my iPhone. In the end the upgrade worked and no data was lost. However, it took me half as long to back up and upgrade a 400-node Linux HPC cluster from SLES9 to SLES 10.

This slow sync performance is not something that just happened to me recently. The very first time I tried to backup my phone, the process took over six hours. At that time I owned the phone for just over a month and had very little data on it beyond the base OS and standard apps. I know there are insane people out there who have ten million SMS messages on their phones, along with twenty gigabytes of photos of their cats. I am not that case. Am I doing something wrong? I don’t know – maybe – but in defense of my credibility I will mention that I have over fifteen years of experience as programmer and Unix system administrator.

To date I have not encountered a computer-related problem I was not able to fix or at least explain. iPhone-iTunes backup duo, however, is a complete mystery to me. Over the years I have used a number of mobile devices – cell phones, PDAs, tablet PCs – that needed to be synchronized with a computer. In every case the backup operation took a fraction of the time needed to backup my iPhone 3GS.

Based on my years of sysadmin experience, I suspect the cause for the slow backup process is not in the amount of data in terms of gigabytes on your iPhone. I think the real culprit is the indexing method used by iTunes to sync data between the PC and the iPhone. For whatever reason, iTunes uses iPhone’s own small CPU to do most of the heavy lifting. Slow iPhone backups are experienced by both Windows and Mac users, so this issue has nothing to do with the host OS or architecture. The problem is definitely with iTunes and how it handles the backup process.

Another possible reason behind the slow backup problem are the crash reports. Remember that Apple advertising campaign: “It Just Crashes”? Maybe it was “It Just Works”? I don’t remember exactly. But in any case it does crash quite often and every time your iPhone poops its pants, it generates an error report. During the backup process those error reports are sent to Apple. One at a time. Every report is sent to the Apple server on an individual basis. That server is overloaded. iTunes patiently waits for the server to acknowledge receipt of the error report and then it sends the next crash report. This ridiculous process can take hours. What prevents iTunes from downloading all crash reports at once, compressing the files and uploading them to Apple as a single archive? Probably very poor programming skills of the idiots who wrote iTunes. Just a guess.

This particular issue can be fixed (sort of). Here’s what you do:

1. Start iTunes
2. Click Edit -> Preferences -> Device -> check “Prevent … from syncing automatically” (see screenshot below)
3. While still in the Preferences window, click Advanced -> Reset Warnings -> OK (see screenshot below)
4. Connect the iPhone to the computer
5. Under “Devices” section on the left find your iPhone and right-click on it (or CTRL-click on a Mac)
6. In the pop-up menu select “Reset Warnings” (see screenshot below)
7. Disconnect iPhone from the computer
8. Re-connect iPhone to the computer
9. Run sync. Hopefully things will go a little faster for you this time. Do use the “Reset Warnings” button from time to time.

Eventually I was able to complete the OS4 upgrade and it only took nineteen hours and fifteen years of Unix sysadmin experience. There were surprisingly few problems after the upgrade. One thing to watch out for: the iPhone seems to forget your voicemail pin. If you can’t remember it, you will have to spend about twenty minutes going through an elaborate system of psychological torture – the AT&T customer support. Well, at least its not Verizon customer support…

Another weird problem that cropped up: an intermittent problem downloading my emails. From time to time I would get an error message saying that I did not provide a password for one of my email accounts. Even though there is a password in the email setting. Re-entering the password did not resolve the issue. At this point I am not certain if this issue was caused by the OS4 upgrade, or if there is a problem with the mail server.

All in all, the OS upgrade would have been a relatively uneventful process if it wasn’t for the slow backup issue. This has been a major problem with the iPhone ever since its market debut. It is difficult for me to believe that Apple cannot fix this issue with relative ease. Just how many programmers does Apple have working on their iTunes software? Two? Maybe they should hire two more.