The audiobook files that I transfer to my Nano (Gen1) do not play continuously.

When one file finishes, it starts to replay rather than move to the next file in the playlist.  Each file indicates that it is "1 of 1".  Happens with MP3 and WMA files and has been happening for several years.  I always need to advance the file manually. 

The repeat function is on, but not the repeat.
What?  That doesn't make any sense.
Have you tried grouping your audiobooks together into playlists to see if that helps?  See this page for more assistance and information on audiobooks for iPods.
http://samsoft.org.uk/iTunes/audiobooks.asp
B-rock

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