Ramblings…

This post documents issues I experienced upgrading a 5G iPod with Firmare 1.2 via iTunes 7. It does not cover any other generation of iPods or any other iPod issues. If you are experiencing problems with your iPod and/or iTunes, I recommend visiting the forums on iLounge or the Apple Discussion Forums.

09/20/06 UPDATE: Apple has begun publishing tech support documents to address some reported bugs in iTunes 7.

09/24/06 UPDATE II – A SOLUTION!: Intrepid reader Ben solves the issue. It works like a charm. Scroll down to his comments, and follow his directions! It worked like a charm for me! Way to go, Ben! My new hero!

12/10/06 UPDATE: Apple releases firmware version 1.2.1. I also did a little experimenting and discovered a simpler solution to the updating issue.

02/02/07 UPDATE: iTunes 7.0.2 and Microsoft Vista compatibility issues.

03/05/07 UPDATE: Apple releases iTunes 7.1, adding support for Apple TV and also supports a new full screen Cover Flow and improved sorting options.

07/01/07 UPDATE: There has been reports that iTunes 7.3 is causing issues. Check out the Apple Discussion Forums about iTunes 7.3 can’t save library (Unknown error -50) .

07/11/07 UPDATE: Apple releases iTunes 7.3.1. According to Apple, “iTunes 7.3.1 addresses a minor problem with iTunes 7.3 accessing the iTunes Library.”

09/10/07 UPDATE: Apple releases iTunes 7.4.1. The release notes state, “This update adds support for the new iPod nano (third generation), iPod classic, and iPod touch, plus create customer ringtones exclusively for iPhone.”

09/17/07 UPDATE: Apple releases iTunes 7.4.2. What’s new in this version: “iTunes 7.4.2 addresses an issue with creating ringtones using iTunes Plus song purchases and includes bug fixes to improve stability and performance.”

09/27/07 UPDATE: Apple releases iTunes 7.4.3: iTunes 7.4.3 addresses issues with the initial setup of the iPod touch on some international versions of Windows.

11/07/07 UPDATE: Apple releases iTunes 7.5, which contains some significant new features and updates. This iLounge articles explains in great detail all the changes included in this version.

11/11/07 UPDATE: Read about my experience “jailbreaking” the iPod Touch.

04/04/08 UPDATE: The latest version of iTunes is 7.6.2.

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I’ve been using iTunes since version 3 – I believe – and never had any serious problems with it. Sure, there were annoying things about the program (mostly how bloated and slow its become since version 5), but no show stoppers. That all changed with iTunes 7. Below is a list of issues that I’ve experienced since installing version 7 Tuesday night.

First Issue
After completing the installation, iTunes 7 would not recognize my iPod (Video/60GB/Black). After a little searching, I found this article on Apple’s support site. The solution was simple enough and it was not a catastrophic issue. Everything looking good.

Second – and the main and major – Issue
Starting with this release, Apple made it so that the only way to update your iPod’s firmware is through iTunes – there is no longer a separate download for a firmware update. Unfortunately, iTunes does a terrible job of installing the new firmware. In fact, it does such a horrible job that your iPod is not updated at all, and iTunes sits there infinitely with a dialog box that says “Updating iPod …” instead. The first time this happened, I let it run overnight just to see if it was just a slow process. If only. The only way to cancel the “update” process is to kill iTunes via Task Manager. I uninstalled/re-installed iTunes, rebooted, and all the other normal things you do on a PC when something acts up. No luck. I posted a plea for help on the Apple Discussion Forums and iLounge. No replies. Through some sleuthing, I was able to uncover the website from which iTunes downloads the firmware update. Fortunately (or not, depending on your point of view), I was able to browse to the site using Internet Explorer and download the update. Unfortunately, the firmware files were not in a form that can be easily installed manually. Or, I just don’t know how to install the file into the iPod. The update was not a simple executable. So, still no help, luck, or mana from heaven. I finally found a clue while searching through Digg. Apparently, I’m not the only one who is experiencing this problem. The comments section of the post provided a link to this (possible) solution. I eagerly – and carefully – followed the instructions … No Luck. iTunes still ejects my iPod and hangs on that damn dialog box.

At this point, I’m between crying and tearing my hair out. After the wife insisted I take a short timeout, I decided to poke around my computer and discovered that iTunes does manage to download the update and store it in the Windows temporary directory. This still does me no good, as I can’t install the file myself, but at least I’m making progress, I think. All this took place over two days, and on this, the third day, I’m still without a solution, and this experience has made me resentful of Apple. Not only has iTunes become more bloated and hogs up ever more resources, but now a major functionally simply does not work. I love my iPod and I think Macs are nifty machines, but Apple – and this pertains to Quicktime also – cannot write Windows applications worth a damn. Steve Jobs should take some of that money he’s making hand-over-fist from the iPod and hire some programmers from Microsoft to write all of Apple’s Windows applications. Some have argued that I would not be experiencing these issues if I was using a Mac. Indeed that may be so, but that’s no excuse for poorly written software. If Apple wants to make something available to PC users, then it should do it well and not offer second-rate products to non-Mac users. Many other people have complained about a multitude of other issues, both with iTunes and the new firmware. So perhaps its a a good thing I don’t have the update, but I should still be able to install it without problems if I want to.

Third Issue
This is minor and more of an annoyance. With iTunes 7, you have to have your iPod connected to the USB cable first before opening iTunes. Otherwise, iTunes will not recognize the iPod. This is not the case with version 6. Also, once you eject your iPod and close iTunes, re-opening iTunes will not cause the iPod to mount. Instead, you have to unplug the iPod from the cable, plug it in again, then re-open iTunes. With version 6, you can re-open iTunes and the iPod will mount. I have the “Enable Disk Use” option selected, so this might not be an issue if that option is not used. I also do not recall how it worked previous to version 6.0.5, so it is possible that version 6 was broken, and version 7 fixed the behavior.

The Upside
Nevertheless, there are some good things with version 7. I like the new pretty icons (I’m a sucker for pretty icons), and I love the new way to browse your songs by album cover – eventhough it smells like a copy from Microsoft’s Windows Media Player 11. I also like how iTunes will now automatically download album covers. This features comes a bit late for me, as I had already spent 6-months diligently finding artwork for each song in my collection, album-by-album. [iTunes is either an OCD's worst nightmare or dream come true]. I also enjoy the new way iTunes displays information on its left-hand pane, although I dislike how music videos can now only be represented by a Smart Playlist. A feature many other users are excited about – but which I am nonchalant – is Gapless Playback. I had to have someone explain the concept of gapless playback to me. I’m still not sure why it’s such a big deal. Oh, well. So, if anyone happens to stumble upon this article and know of a solution to my issue, please let me know. I’m going nuts over here.

UPDATE – 09/14/06 at 10:33 pm
After work, I had the brilliant idea of installing iTunes on my wife’s laptop. If it won’t install on my laptop, then maybe a fresh install on a clean machine will do the trick. The result? . . . No luck (again). I got a step further – iTunes actually showed a dialog indicating it was downloading the update and displayed the release notes, but then the same result (stupid dialog box). Really, the only thing left for me to do is to restore my iPod. I loathe to do this, as it is the “nuclear” option. Also, I would be even more peeved if, after going through the trouble of wiping my iPod, the problem still persists. However, the fact that a fresh install of iTunes on a clean machine does not resolve the issue makes me believe the problem is with the iPod, not the computer(s). Also after work, I searched through the iLounge forums again and found this post. I tried it and (you guessed it) no luck. I checked out Apple’s Discussion Forums again, and found this post. I haven’t tried it yet, and I’m not sure I will. At this point, I’m thinking that I should just wait and see if Apple will release an update in the next few weeks. Except for the firmware updater, Version 7 works fine in every other respect. Surely, Apple cannot ignore all this uproar. If an update is released, and I still experience issues, then I will go nuclear. Sigh.