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iPod Classic 6th Generation. Model A1238 / 80, 120, or 160 GB hard drive / black or silver metal front

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Most songs won't play and skip. iPod will not synchronise.

Most of the songs wouldn't play on the iPod, as though they were corrupted. However, all tracks play fine via iTunes. I've tried resetting the iPod and eventually decided to restore it. Now, when I try to sync with iTunes, around 400 songs transfer then syncing suddenly stops and an error '(-50)' pops up and causes iTunes to crash. I unplug the iPod and iTunes resumes working normally and the iPod remains to have no content synced to it.

I'm running Windows 7 Ultimate 64bit and iTunes 10.4.1.10. iPod software version is 2.0.1.

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Try to place your iPod in Disk mode and see if you can format the iPod as a drive. I have a feeling its your HDD but try it. Before placing the iPod into Disk Mode, verify that it is charged.

Toggle the Hold switch on and off (set it to Hold, then turn it off again.)

Press and hold the Menu and Select buttons for at least six seconds, until the Apple logo appears.

When the Apple logo appears, release the Menu and Select buttons and immediately press and hold the Select and the Play/Pause buttons until the Disk Mode screen appears.

Illustration of disk mode

Connect the iPod to your computer; the screen on the iPod will should say "Do not disconnect".

From here Also, try the diagnostic mode and see what it tells you.

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OK, I tried this and thought I was getting somewhere. The songs stopped syncing at 434 of 2693 this time. Two minutes later, iTunes crashed again. Thanks for your help. Any more suggestions would be much appreciated.

Edit: Error has changed to (-53) now. Message stayed the same.

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Check on here for your previous -50 error have you tried to sync other songs? Now I am wondering if this is not an iPod but an iTunes error....does your iPod respond properly in the Diagnostics and disk Mode?

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It also appears that you are not the only one. As suggested here one more trick to try is to delete your iTunes library and start from scratch and see if iTunes library is corrupted. If that does not work I think you are do for a new HDD

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Thanks a lot for your help. I've tried all of your suggestions, but unfortunately I can't fix it. :( I guess I'll be buying a new HDD for it soon.

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Michael, most of the times it is the HDD. Not a terribly difficult or expensive repair. Also, change the HDD cable.

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Michael will be eternally grateful.
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