Problem getting Videos to play back to back...

I have ripped some Music Video from DVDs and my ipod will play them fine. It just wont play them back to back. Thus in a playlist it just plays the videos that I have bought from Itunes. I can manually play the videos (ripped) but it always only then plays the others I bought and ignores the videos I have placed on the Ipod..
Any help out there..
thanks
Mark

The process is the same but the constraints are slightly different - there are plenty of threads on the subject and as long as the video complies with the specification below, it will transfer. If it isn't transferring then there is something out of spec for that particular video.
H.264 video up to 720p, 30 frames per second, Main Profile level 3.1 with AAC-LC audio up to 160 Kbps, 48kHz, stereo audio in .m4v, .mp4, and .mov file formats; MPEG-4 video, up to 2.5 Mbps, 640 by 480 pixels, 30 frames per second, Simple Profile with AAC-LC audio up to 160 Kbps, 48kHz, stereo audio in .m4v, .mp4, and .mov file formats; Motion JPEG (M-JPEG) up to 35 Mbps, 1280 by 720 pixels, 30 frames per second, audio in ulaw, PCM stereo audio in .avi file format

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