So I picked up my new 5th gen 80g ipod last night (upgrade from a 3rd gen) and got all my music transferred over without a problem. I decided to mess around with the video. Keep in mind that I first set up the new ipod on my PC using XP. I found some program called DVD to Ipod by Cucusoft and tried it out and worked great, but it was only a trial and leaves watermarks on the video. I'm not really ready to spend $40 on the software. In any case, I was able to easily transfer the video from my iTunes video library to my ipod. No problems. I was reading this forum and it seems that handbrake is highly recommended and it's free. So, using my also very new MBP, I installed handbrake and ripped an episode of The Office to my mac. No problem. Imported the video into iTunes without a hitch and it plays just fine within iTunes or outside of iTunes. So I try to drag it to my ipod and it gives me an error saying it can't copy the file to the ipod because the ipod can't play that format or something! It's a friggin' h.264 video I created using guidlines from this forum. Anyway, I went into the video file's info within iTunes and tried switching it between TV Show and Movie categories, but the ipod still wouldn't take it. I had the bright idea this morning that maybe it had something to do with the fact that my ipod was originally set up under windows. So I dropped the Handbrake encoded video onto my PC and tried again. I didn't get any errors when I drug the file from my Movies library to the ipod, but when I checked my ipod to see if it was there it had nothing in TV Shows, Movies, Podcasts, Library, nothing.... but no errors! I tried again with the rip I did last night with the trial PC software and no problems at all. Am I missing something here? I'd really like to be able to put my DVDs on the ipod without having to spend even MORE money if possible. Sorry for such a long explanation, but hopefully I gave enough details.