Ipod Classic Won't sync my music because it can't find a file or disc

I have the 2006 30 gig ipod classic( i dont know what generation that is) but i have just restored it to factory settings, and everytime i plug it in to sync music, it just says "cannot find file" with a big red x, or "cannot find proper disc", i dont know what the problem is but it uploaded about 187 songs and i have atleast 1100 more to go and it just stopped their, if you could help me out i'd really appreciate it

I would try restoreing the iPod to factoery defaults/new iPod and try again.

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