Syncing iPod Touch Causes External Drive Disconnection

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This is a really bizarre problem. I am unable to sync my iPod Touch. Once it goes to copy the first song (whatever it is -- this is not a file issue), my computer ejects my external hard drive and stops the sync. It then takes roughly 5 - 10 minutes to finish the sync (though put no new material on it).

I have to unplug my external drive then replug it to be recognized.

I've tried removing all music from iPod, which worked fine. But now I still can't put anything on it. I checked and have the latest software on both iTunes and the iPod. I've done simple stuff like restarting. Any ideas?
 
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Your Mac's Specs
mid '09 13" MBP 2.53 C2D, 8Gb RAM, 250 Gb HD, SL and Win7
Are they connected to separate USB ports on your Mac or are they both connected to an external hub?
 
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my ipod has began to do the exact same thing.. and I'm not even using an external hardrive.. I need help also.. I keep getting errors saying that my ipod disconnected even though it didn't
 
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Are they connected to separate USB ports on your Mac or are they both connected to an external hub?

Separate hubs. I don't think it's a power issue. I've synced this way before for a year or so, and I'm able to play music for as long as I want to (as well as edit photos that are on the external). It's just that as soon as I try to sync -- the first song hits -- boots off the external.

I AM able to sync songs on my hard drive though.
 
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Upon more experimenting, it looks like certain songs are culprits, and usually entire albums. I can locate which ones they are by constant syncing (and disconnecting) but I feel like this is bad for the drive.

Any guesses on what characteristics I could look for on the files that would cause them to behave this way?
 

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