IPod will not take movies

I have a 60gb 5th gen ipod and am using Handbrake to add movies to iTunes for transfer to my iPod. After about the 3rd movie having been added it will no longer upload my movies. I have "selected movies" chosen and have checked the movies I want, but to no avail, accept for a few. They are all pretty close in size, and setup via Handbrake... any ideas here?

Is it possible that you don't have enough memory on the iPod to hold them all?
Also...be advised that the (recently updated) terms of use for the forum prohibit discussions about the following:
"Do not submit software or descriptions of processes that break or otherwise ‘work around’ digital rights management software or hardware. This includes conversations about ‘ripping’ DVDs or working around FairPlay software used on the iTunes Store."
I'd say we may be treading close here...
Diane Wordsmith
iBook G4 (& an iMac running OS 9)   Mac OS X (10.3.9)   iPod Video

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