IPod shuffle causes iTunes to move songs to the trash

When I plug in my iPod shuffle, it causes various files (AAC, pAAC, and mp3) to be move from iTunes, to the trash. Fortunately, I noticed because at the next sync, iTunes asked if I wanted to import the purchased music from the iPod shuffle to iTunes.
Here's the kicker. When I tried to restore the iPod shuffle, I got an "unkown error (1418)". I reset everthing, but still got the error.
Is there any way I can:
1- Stop this from happening.
2- Restore my iPod shuffle despite the error message
Thanks.
iPod Shuffle 1.1.4 Mac OS X (10.4.7) iTunes 7

It could be an indication or a damaged or dying hard drive. I would recommend doing a disk diagnostic on the iPod's HD using the instructions given by turingtest2 in this older thread. He also covers what the resulting numbers indicate.
https://discussions.apple.com/thread/3784647?start=0&tstart=0
If necessary, post the resultings numbers and we can verify what the next steps to take.
B-rock

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Hi, i've also been having a very similar problem with my ipod as well. I find that regardless of which windows-based pc i use (either my xp laptop @ home, or my win2000 desktop @ work) windows and itunes refuses to recognise my ipod. In windows explorer it will show it as a removable drive, but if i click on it, windows freezes. If I try to disconnect it, I cant because windows keeps reporting that 'the device is being used, try disconnecting later' and so then i shut down my laptop to disconnect it safely.
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Okay, I have an Itunes account already and it is connected to my old ipod mini. I recently got an Ipod shuffle and when I try to load songs onto it the ipod shuffle won't recognize them because they are protected on my itunes account. I tried to change my account so it recognized my new ipod shuffle and itunes said I was not authorized to do that. Any suggestions?

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I'm sorry to hear you are having issues with your iPod shuffle. I also apologize, I'm a bit unclear on the exact nature of the issue you are describing. If you are having issues transferring music to your iPod or playing music that is on your iPod, you may find the information and articles linked from the following page helpful:
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IPod shuffle causes iTunes to move songs to the trash

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