Music disappears from iPod Classic after disconnecting from computer

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.

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.

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.