Problem transfering movies

i'm trying to transfer movies to my friends ipod, but it's not letting me. these are movies that i own and have transfered into ipod format. i have the 160gig and my friend has the 30 gig.....in case this matters. is there a setting i need to change? can anyone give me some troubleshooting tips?
thanks

Try the Videora iPod converter from http://www.videora.com/en-us/Converter/iPod/
You can't use the H.264 settings because the iPod doesn't like the non-Quicktime codec, but the highest quality mpeg4 profile works like a charm.

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