TNA.....we had something similar with our ipod classic!!!
what type of file are you trying to import? is it a straight music track or music video? or dvd movie?
I spent just over a week trying to find a program that would convert dvd movies into a format that Itunes recognises....
the only program I recomend you could try is "DVDfab platinum edition", this fixed our problem with dvd movies, as DVDfab converts the file to an mpeg4 format, once this is done you should be able to use itunes to import the file ready for synching, you should need to convert the file again once you have used DVDfab.
see how you go with getting a copy of it.
goodluck (bloody itunes)
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