iPod Classic and iTunes 10.5: Support Observations

Ever since iTunes 10.5 came out with support for “iTunes Match”, I’ve been debating whether I should upgrade my home system. I did a wide variety of web searches, and finally opted to monitoring the RSS feed of the Apple Support community for the iPod Classic. In doing so, I’ve learned a lot…

[Updated 2011-12-16;  2012-01-13;  2012-01-16;  2012-01-25; 2012-02-26; 2012-03-04]

[¶1] First and foremost, I’ve learned that many iPod users (well, at least those that go to the support forums) don’t understand how iTunes and the iPod coexist. There are numerous questions about syncing, and why something doesn’t sync. There are loads of questions on how to move an iTunes library from one computer to another. My advice in this area: Keep your digital music on an external hard drive, and back it up regularly. Also backup your .itl files (iTunes Library Files), and the XML equivalent, and recognize that paths need to stay the same if you want to use the library on a new computer.

[¶2] Second, I’m still unsure about iTunes 10.5 or 10.5.1, and wouldn’t advise moving to it unless you really need it. I’ve seen loads of posts from people using the latest version of iTunes, and the common complaint is that the new iTunes is taking forever to synchronize, or it doesn’t recognize the iPod, or thinks the iPod is corrupt. The problem appears to be (especially on Windows) that antivirus products interfere with the synchronization, the synchronization times out, and ends up corrupting the filesystem of the iPod. The iPod then mounts as a disk but isn’t seen in iTunes, with the usual recommended solution of disabling the anti-virus, doing a CHKDISK of the iPod, and then attempting to restore the iPod. This is a typical response in this vein. Here’s is more useful advice on how to break up a transfer.

[¶3] If you want to try to reinstall an older version (no guarantee it can read the library), try visiting the oldapps page for iTunes. Alternatively, you can visit the Apple Knowledgebase Search function, search for your version, and then restrict the search to “iTunes” and “Downloads”. For example, doing so I found the link to download iTunes 10.4.1 for Windows (64 bit). If you do so, I suggest making sure you have a backup copy of your iTunes database (i.e., the .itl, .itdb, and .xml files in your iTunes directory), and that you have completely removed iTunes following these instructions from Apple. It probably wouldn’t hurt to have a complete backup of your music files as well, but I’m sure you do that already. If not, here are instructions on how to backup your music to an external drive.

[¶4] ETA: Another interesting data point: If you just disconnect, the archive bit could be set resulting Windows to ask you to “Scan and Fix” the iPod. Here’s what to do if you get that message.

[¶5] For a lot of other problems, it seems that people still don’t know about the “5 Rs”. In particular, rebooting the iPod (I find) tends to be the answer for click-wheel slowdowns. Don’t know the 5Rs? Look here.

[¶6] When something goes wrong, ask yourself: Did it work before? What changed? Sometimes that can give you the clue. If you updated your iTunes, that could be the underlying cause. Although you might have to restore your iPod, you should consider going back to an older version of iTunes. This points out two other another important rule: (1) Always back up your iTunes database before you update iTunes, and (2) Always make a copy of each iTunes software download, so you have it in case you need to go back.

[¶7] I’ve learned there are some hidden modes on the iPod Classic. In particular, there is an iPod diagnostic mode. I haven’t experimented with it yet (although I will if there is a problem). This post on the forum talks about the mode. I’ve also found articles on the mode here and here. Another good discussion of disk diagnostics is here.

[¶8] A common query is how to move music from the iPod back to a computer. A lot of people refer to this post on the forum (written by forum regular Zevoneer). Myself, I’ve had good luck with Copytrans, or you can just find the music files and add them directly (of course, then you lose ratings and play counts).

[¶9] A similar common query is how to move music to an external drive. This support article indicates how. If you want to understand things better (or are moving between operating systems), this article from iLounge provides a real good explanation about how to move media the right way.

[¶9.5] Backing up your music is an important thing to do. iLounge has an excellent article on the subject: The Complete Guide to Backing Up your iTunes Library. Read it. It describes the structure of the library and how to find your files. There are lots of ways to do it: Use your backup program to backup your music files and your iTunes directory; manual copying; etc. Here is one user tip from the iTunes forum for backing up; I haven’t tried it yet. However you do it, do it regularly and to a different drive than your main music drive.

[¶10] An iPod displaying a Red X is a bad thing. In almost all cases, it appears to be a hard disk crash. Alas, the answer for that is either Apple Service, or just buying a new Classic. Here’s what Apple says. Some suggest attempting to realign the head by a gentle slap of the iPod against your thigh. It is important to remember that an iPod Classic has a spinning hard disk, not a solid state disk. Sharp bumps, drops, etc. can misalign the heads and result in a head crash, and that’s often all she wrote.

[¶11] It appears that car audio systems, especially those with dock connectors, are particularly bad for the iPod classic. If there is no transformer or fuse in the middle, some of the newer ones can corrupt an older classic. At this point, I’m only sticking with using the headphone jack to connect to a speaker system. BMWs are particularly bad here. Often, the problem is software incompatibility between the car software and the iPod software. Again, the headphone jack and an external charger is the safest approach.

[¶12] Some people don’t know the generation of their iPod. This page can help them find out.

[¶13] What else have I discovered? Error 1439 can be the wrong type of USB port. Error 69 indicates some corruption in the library. Sometimes the only answer is to start afresh–that is, completely erase and reformat the iPod disk, and then restore the iPod to out of the box status and reload.

[¶14] Lastly, it’s a bad thing to drop an iPod Classic. No duh from me: there’s a hard disk in there. But loads of folks drop their iPod Classics, and then post wondering why it is no longer working, and making a clicking sound… Water is also bad, but if your lucky and the amount of water is slight, you might be able to save it using these tricks.

[¶15]Evidently, there is an alternate OS available for some, not all, portable music players. In particular, it does not seem ready for prime-time on the iPod Classic. Information is available at http://www.rockbox.org/

[¶16] Turingtest2 has a nice post explaining how to fix album groupings in iTunes.

I’m posting this mostly for my reference–so I can find these things in the future. They may be of interest to others. For those out there that have iPod Classics (us older holdouts) and Windows 7: How is iTunes 10.5 or 10.5.1 working for you?


10 Replies to “iPod Classic and iTunes 10.5: Support Observations”

  1. I have a 160gb classic ipod which is brand new. When I plug it into my computer, which runs with Vista, it says it needs to be formatted. Itunes also says that it is corrupted. I’ve restored and reformatted the ipod and the same message appears. When I plug my ipod into a different computer it works fine, and when I plugged an iphone into my computer it was recognized by the cpu and itunes. What can I do next?

    1. Don — If you read the Apple Support forums, you’ll see that this is a quite common occurrance, especially (seemingly) since iTunes 10.5 has come out. If you have a brand new iPod, probably the easiest thing to do (especially if you have a laptop) is to take both the iPod and the laptop to the genius bar at an Apple Store (make an appointment, and allot plenty of time so you’re not rushed). You’re under the original Apple support period, so use it.

      Some of the notions I’ve seen as possibly causing this are:

      • iTunes. My favorite suspect for everything. I think iTunes 10.5 does not work well with the iPod Classic, and I personally haven’t upgraded (and haven’t seen any of these issues). You might consider removing everything Apple and reinstalling 10.4 (there are links in my post for doing both).
      • USB Drivers. This relates to the above. The Apple device driver could be flakey, or it could be interacting with other USB drivers on your system. There could also be a problem if you are connecting through a lower power USB port (the rear port on a Macbook is notorius for this) or an unpowered USB hub. If you are using a hub, and there’s lots of traffic to other devices on the hub, this could also be the problem.
      • Cockpit Error. A number of people are corrupting their iPods by not ejecting them through iTunes first. That can be a big problem.
      • Hard Disk Errors. I’ve seen some that suspect that newer-manufactured iPods are having more hard disk errors. I don’t think there’s enough data to support that theory yet.
      • Antivirus. I’ve seen some that believe it to be an interaction between antivirus and the iPod classic. I don’t believe this: I’ve never had my AV scan my iPod, and I would think it would interact with other devices.

      Given that you indicate your iPod works when you connect it to a different computer (presumably, with a different instances of iTunes), and that the iPhone works with the current iTunes on your Vista machine, I’d suspect that the USB driver for the iPod Classic that came with 10.5 for Vista isn’t working right. I’d start trying to move down the iTunes chain starting with a 10.4 version until I found a driver that works reliably. If you need to use your Vista machine with both the Classic and the iPhone, then I think Apple Support is the answer.

  2. Hello, I’ve got a new computer as my old one broke and am unable to use the harddrive to gets old fles off. I have installed ITUNES on new computer for the time being, but I did have music and books that were not purchased through ITUNES, anyway the laptop and ipod sync’d in error and have now lost all music and audiobooks etc, is there anyway this can be reversed?

    1. If the music has been deleted off the iPod, the likely answer is: no. You might be able to find a company that can do data retrieval from failed disks. One other option depends on how the old computer broke. If it wasn’t a hard-drive problem, you might be able to find someone who could install the hard driver from the old computer into the new computer (or into an enclosure such that it could be connected by USB) — this might allow you to get the old data.

      This is a demonstration of how important it is to (a) keep your music files on an external hard drive, so the computer crashing doesn’t affect those files, and (b) to have a backup, backing up your hard drives to yet another external hard drive. If you trust the cloud, backing up to the cloud is also an option.

      I’m sorry, but there’s not much more I can suggest.

  3. Apple in my point of view sucks wouldn’t it be much easier to buy a mp3 and download all the songs that you get on itunes for free online?

    1. The question is not whether Apple sucks. There are people that, for whatever reason, have purchased Apple products (in particular, here, the iPod Classic) and then need to use iTunes to move music to the iPod.

      The issue is also not buying mp3s. There are many ways to get music into iTunes, least of which is purchasing through iTunes. You can buy mp3s through Amazon (which is what I do, so I don’t have the digital protection). You can rip from CDs. You can record from LPs. However, you get your MP3s, you need to move them onto the Apple device, which is done from iTunes.

      Please separate the acquisition of music from the loading of the device.

    1. That I don’t know. I”m sure you could make appropriate files available (.mp3, .wav), but you’ll need to modify your .htaccess file (or equivalent, depending on your webserver) to know the file mime time to tell visiting browsers so that the file can play. If you are using WordPress, you could see if there is an appropriate plugin.

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