You may try restarting and reconnecting all devices in the setup altogether.
There can even be issues with the nano's touchscreen.
There can be times when the nano restarts very often.
In such a situation, it is suggested to restore the i Pod when in disk mode.
There are many, probably too many, programs already available.
I prefer to use VLC to convert to i Pod video, because I know that if VLC can play the file, then VLC can convert it for my i Pod.
Whereas a person can store their entire music library on an i Pod, a person will not be able to store their entire video library on an i Pod.
At some point, that person will need to come home, dock the i Pod, and transfer files.
It is more likely that a movie, a music video, or at most a complete television series will be stored on the i Pod. Please be sure you are using the default settings for VLC. Look for the part that has #transcode, and type width=320,canvas-height=240 somewhere inside the . This setting changes the width to 320 pixels and adds black bars above and below the movie, allowing all movies to maintain the appearance of their original aspect ratio. If you change any of the settings below this box, you will have to re-enter the width and height settings.
Please be especially sure that you do not have "repeat" set, as you will infinitely overwrite your transcoded file. So far, everything is fairly standard, but here comes the tricky part. Click OK to close the Stream ouput dialog, then click OK to close the File open dialog.