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I've got a somewhat puzzling problem here (or at least, I find it puzzling).
I'm going to go into great detail in the hope that it helps someone to point me in the right direction, and also in the hope that a potential solution might help someone else in the future - so please forgive me if some of the info here might not turn out to be relevant to the problem!

TL;DR: When disconnecting the iPod from my Mac (after ejecting from iTunes) the iPod thinks there is no music on it.
If you get bored by the details, please scroll down to the bottom for a summary of what I've done to try and fix this.

Background

I have an iPod Classic which I bought just under a year ago.

I use the iPod almost exclusively connected to the aux input of a car stereo (aboard a boat, actually), rather than with headphones.
I normally charge it via the USB mode of the same car stereo.

Every now and then, the iPod freezes. In particular, it very often freezes when plugging it into the stereo (USB mode) to charge, or when unplugging it. I simply reboot it (or reset, as Apple like to say) by holding down the play and menu buttons, and then all is well.

Recently (in the last couple of weeks) the iPod started to reset certain settings whenever it froze and had to be rebooted. After every reboot it would ask for the language to be set - something it never used to do - and it also sometimes reset other settings; such as enabling the clicking sound when scrolling.

The Problem

Yesterday, I plugged the iPod into my MacBook Pro (Late 2008, OS X Lion 10.7.2, iTunes 10.5.3), to transfer (I manage the iPod manually rather than with auto sync) some new music from my iTunes library.

When I finished, I ejected the iPod from within iTunes, as usual, and then unplugged the iPod when it told me it was ok to do so.
Rather than going straight to the music screen, as usual, the iPod rebooted (reset) itself. As I mentioned above, the iPod is sometimes a little strange about rebooting so I didn't think anything was strange. But...

When the iPod came on again, it had no music on it! Nothing. It appeared to be empty. Looking in the Settings->About screen, I could see that in fact the amount of space corresponding to my files was still being used - the hard drive hadn't been wiped, but rather the data, or the iPod's database, had presumably become corrupted in some way.

Fortunately I have all of my music on my Mac in my iTunes libraray, so this wasn't a total disaster. I thought I'd simply have to restore the iPod to factory settings and then put all my music back on. How naïve of me. I should know better.

When I plugged the iPod back into the computer, it didn't appear in iTunes. After some time, it appeared in the Finder, and iTunes froze. Ejecting the iPod took ages, and looking at it with Disk Utility caused Disk Utility to freeze. Odd.
I also tried opening exPod, just to see if it would work - but no; it also froze.
No combination of rebooting the iPod and computer, relaunching iTunes, etc, would make the iPod show up in iTunes.

Trying To Fix It

The first thing I tried was the iPod's built-in diagnostics, started by pressing menu+left whilst booting. But it couldn't find anything wrong.
I also tried starting the iPod in disk mode - it didn't help.

After everything else I could think of - including everything in Apple's awful support site, and failing to find anything relevant via Google - I eventually resorted to this technique (reformatting the iPod with Disk Utility), supposedly "The Super Fix for Most iPod Problems".
Actually I wasn't able to reformat the disk from Disk Utility, due to POSIX permissions errors, but I did eventually manage to format it from the Terminal using diskutil. And before you ask, I used the Extended Journaled format, with Apple Partition Map - as the iPod was previously.

And this fixed the not showing up in iTunes problem - I was able to restore the iPod from iTunes, and then add some music to it.

But guess what? Right. When I ejected it, it did exactly the same thing as before: the music all "disappeared", and the iPod wouldn't show up in iTunes.

More Attempts At Fixing It

Well, as you can guess, I was getting pretty fed up by now... But what could I do but keep on trying?

My next step was to format the hard drive as FAT32, from Disk Utility, and then initialise the iPod from iTunes as if it were a new iPod. This resulted in iTunes identifying the iPod as a Windows iPod, though in fact I had never connected it to Windows.

Now I tried adding content again, and this time, it actually worked! When I disconnected my iPod after adding one album to it, the album stayed on it!
Phew. Problem solved, I thought. Me being naïve again...

So, I proceeded to copy a few tens of gigabytes of music to the iPod, then I disconnected it - and we were back with the same old problem. F*ck. :'(

So, my final brainwave (well, maybe not...) was to actually format the iPod from Windows, via Parallels.
Unfortunately, I was unable to make iTunes on Windows download and install the firmware, but I did the next best thing. Just like above, I formatted the iPod as FAT32 from Disk Utility and then initialised the iPod from iTunes on OS X, resulting in an apparently "Windows-format" iPod, and then instead of adding music from my Mac, I connected it to Windows and added music from there.

So far (touch wood) I haven't had the problem when disconnecting from Windows.
So, I'm assuming this is a problem on my Mac (ie, in OS X) rather than on my iPod.
UPDATE: I have now had the same problem on Windows, so I guess this is an iPod problem.

Summary

So, to summarise the problem and the step sI've taken to solve it:

  • When disconnecting the iPod from my Mac (after ejecting from iTunes) the iPod thinks there is no music on it.
  • When connecting the iPod to the computer again after this, it doesn't usually show up in iTunes. Occasionally it does show up, and iTunes says it is corrupted and needs to be reset.
  • Formatting the iPod from Disk Utility and then restoring, or simply initialising, the iPod from iTunes doesn't solve the problem - it makes the iPod show up in iTunes again, but the problem occurs again as soon as I disconnect the iPod again.
  • It doesn't make any difference if I format the iPod as HFS+ Extended Journaled or as FAT32.
  • Managing the iPod from Windows, however, seems (tentatively; ie thus far) not to cause the problem.
    UPDATE: I have now reproduced the same problem via Windows.

So, what is the problem?

So, based on all the above, it looks like probably a problem in OS X. But I haven't been able to find out where the problem would be, or even for sure if it is an OS X problem.

I'd tentatively guess that it might be a problem with /System/Library/Extensions/iPodDriver.kext, but I don't know how I can check that (removing iPodDriver.kext stops the iPod from showing up in iTunes at all, and I don't know where I can get a "clean" iPodDriver.kext to replace it with).

UPDATE: I have now had the same problem on Windows, so I guess this is an iPod problem.

If anyone has any ideas, or can point me in the right direction, I'd be really grateful. I've reached the end of my troubleshooting abilities, and am at a lost end as to what else I can try.

Oh, and thanks for getting to the end of my monumentally long post! :-D

System Info

Mac:
  • MacBook Pro, Late 2008
  • OS X Lion 10.7.2
  • iTunes 10.5.3 (yes, I know there is a newer version. I'm trying to download it, but havent had good enough internet yet)
iPod:
  • Firmware 2.0.4 (latest version)
  • Model MC293
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2  
If anyone is looking for an example of how to ask a troubleshooting question, here is the canonical Way To Do It! Well asked. –  Daniel Lawson Apr 2 '12 at 15:54
    
Thanks @DanielL! :blushes: –  caesarsgrunt Apr 2 '12 at 15:58
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5 Answers

Given your problems, I think it's extremely unlikely that this is a problem with Mac OS X, even though you haven't yet reproduced the same error with Windows. While not beyond the realm of possibility, it seems extremely unlikely that a failure in Mac OS X would only affect one device, and in such a specific way.

You mention you bought this just under a year ago. If so then it's still under warranty. I suggest returning it to Apple and getting it replaced, it sounds like you've having serious problems with this device. Describe the problems you're having, or, if you can, demonstrate it to them, and they'll most likely replace it.

The only reason I can think why they would not is that you mentioned you use this device on a boat - if it got splashed, that would be considered "liquid damage" and is not covered by the warranty.

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Thanks for the quick answer! The iPod certainly hasn't been wet; I've always kept it inside the boat. I guess it's a damper atmosphere than being on land, but I haven't had problems with other devices including computers which have been used aboard daily over a period of many years. I will try finding an Apple store and taking the iPod in - but the problem is that I'm abroad at the moment. I don't know what effect that has on the warranty. I won't be back home before the warranty expires... –  caesarsgrunt Apr 2 '12 at 15:48
    
@caesarsgrunt I'm pretty sure any store will do. If you bought directly from Apple you don't even need a receipt - they can just look up the date of purchase on their system. –  Kyle Cronin Apr 2 '12 at 15:54
    
Unfortunately I bought it from Carrefour in France, but I do have the receipt (I think...). I'll try and find out about my nearest Apple retailer. Thanks for your help! –  caesarsgrunt Apr 2 '12 at 15:56
    
Just an update to say that you're right; I have now reproduced the same problem from Windows. According to Apple's website my warranty has expired "based on the estimated expiration date", but my receipt indicates that I purchased the iPod mid-May 2011. I guess I just have to show the receipt as proof in an Apple Authorized Service Provider. –  caesarsgrunt Apr 2 '12 at 17:11
    
@caesarsgrunt I think Apple's site bases the warranty off of when the iPhone was sold to the reseller, but I'd imagine they'd honor a replacement if you had a receipt. Good luck! –  Kyle Cronin Apr 2 '12 at 17:59
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So i was having the same problem over and over again after using the Erase thing. So I read your whole thing in frustration and tried things til it worked for me. And my solution might be something you've essentially tried, but I might as well tell you cuz I had thought I'd done this too.

Put your iPod in DISK MODE and connect to disk utility, then erase it. Unplug it. Plug it back into iTunes, restore it. Eject it after it's all restored and updated. Plug it again and add something small.

The key for me was I had "Formatt[ed] the iPod from Disk Utility and then restor[ed], or simply initialize[ed]" like you did, but it wasn't in Disk Mode when i did it. So i added a whole library, and it I thought it had worked (the whole reason I had "erased" it was cuz it would freeze every time it synced) - but then I saw nada.

Hope this works for you!

Here are the instructions again so you don't miss anything.

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Welcome to Ask Different! While the link you posted may answer the question, it is best to summarize the contents of the link in your answer, then provide the link for reference. Links have a tendency disappear over time, leaving a non-applicable answer for those who may stumble upon your answer in the future. –  daviesgeek Jul 19 '12 at 21:23
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up vote 0 down vote accepted

For what it's worth; this eventually turned out to be a hard disk issue.

I had the hard disk replaced and it has performed fine since.

I must say, I am still surprised that a hard drive issue could have these particular symptoms. I, and various people I showed it to, thought it must be a logic board problem.

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I have an alternative take on this problem:

I have just bought a Classic 160 Gb at Amazon few weeks ago and I have been facing the same issues as you.

I do not use Mac OS X, nor iTunes to sync. I run Linux and I use Media Monkey on a Windows VirtualBox Machine.

During the past two weeks I have tried everything that I could find. iTunes have not even been able to read my entire collection (strange, right?)

My findings

I have just restored the iPod firmware a few minutes ago. Started MediaMonkey and sync'd 10 songs from an ordinary random artist. Disconnected and the songs were there, nice. So the iPod is actually working. So far, so good, I have figured that out before.

However, in the meantime, while I was checking my library, I recalled that I have some songs from Japanese bands with Japanese characters in their names. Historically, this would be very error prone. So I did gave it a try, and sync'd 64 songs from that band. Disconnected the iPod and the songs were all gone.

So apparently the 2.0.4 firmware does not handle these characters very well. Check your library, make smaller tests. I am about to restore the iPod again and will try to sync some more files with normal ASCII characters. Will update you.

My old, now dead (waiting for a new disk), iPod, running 1.0.2 was able to hold those files nicely.

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SOLVED. Turns out that the problems were not with special characters. After my post, I made some additional tests, and suspected from some incompatibility between Media Monkey and the version of the iTunesDB, but I disregarded that in sequence. My last attempts would be to either try to sync using a native MacOS or Windows instead of a virtual environment...and...bang! it worked. I took another notebook running windows, installed all software, imported my library, sync'd the ipod and now I have my songs back on the car!! =) –  william Dec 3 '12 at 14:43
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That's exactly the problem I have been having with my 120g iPod Classic. It seems you have figured out the problem now, but just in the case of others having the same issue, I will second your story with my situation.

My iPod is about 5 years old now. In the first year, it started having issues and I took it to Bestbuy (where they are not allowed to touch ipods out of warranty and the only thing they can do in warranty is send it back and get another one) and since I knew the employee that was working there at the time, she told me all I needed to do was restore it. So...I went home and did as she said. It worked fine for about 2 weeks afterward and then it had a frown face when I plugged it in. (not the red frown just a frown next to where my iPod was...this was a few years ago)

So I restored it again. Then I added all of my music to it and ejected it and NOTHING was on it, but the music was still taking up my memory! I restored it AGAIN. Nothing. I put it in my bag to take back to my house. (I was at my mom's) When I got home I couldn't find my iPod. My sister is a known clepto and had been staying with my mom so I figured she had gotten sticky fingers yet again with my stuff-not uncommon. I was even riding with her once and she pulled out an ipod that looked exactly like mine! A year ago, I was cleaning out a bag and low-and-behold my iPod was in the front of it!!! I was so excited! I plugged it into the computer immediately and then I remembered why it wasn't such a loss when I couldn't find it-it was messed up and frustrating to even deal with it. Then my daughter was given an 8g iPod touch for Christmas and my husband and I both have iPhones so I figured if I can deal with these Apple products (I have Windows), I can definitely deal with a measly Classic iPod. So I hooked it to the computer and called Apple Support, who sent me a step-by-step tutorial on how to change the disk and get it to recognize my iPod as more than a "USB storage device." Did this. It WORKED! ...for about a week until I plugged my iPod back into the computer to put more music onto it. Now it's doing the SAME THING. I've tried changing the disk again and it says that it has music on it every time but won't show it on the iPod. I took it to the Apple Store and they had a genius look at it for me and he says that it's most likely a hard drive issue and that the only thing that can be done in this case is to replace the hard drive, which will cost about $130 or I can get a new iPod and recycle mine to them for 10% off of my new iPod. I find it hard to believe that it's just a hard drive issue that can't be fixed. The music is there somewhere. It's also funny to me that this starts happening as soon as the warranty is about to run out almost as if it is programmed to work properly for a year and then you'll have to spend more money on buying either parts for it or a new one. I spent $300 on my iPod with the warranty and all they did when I took it up there when it WAS in warranty was tell me to restore it and now it won't work.

@caesarsgrunt-When you replaced your hard drive where did you get it and was it expensive? I want to replace mine (it will be cheaper) but I don't want to go through the Apple Store.

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