Shuffle showing large song list, but playing only 17 songs ?

My shuffle when connected, shows a list of approximately 50 songs.
The same playlist, when put on my ipod, plays perfectly, but playing from the shuffle will only play about 17 of these songs, and then repeats them over and over.
I have restored it twice, and each time, the same thing happens. The same songs, in the same order, and only 17 of them
We upgraded to Leopard recently, has this got anything to do with it ?

Make sure (by selecting any of the ones that don't transfer) using GetInfo in the File menu that the songs conform to the following:
If you can’t load a song or other item onto iPod shuffle
The song might have been encoded in a format that iPod shuffle doesn’t support. The
following audio file formats are supported by iPod shuffle. These include formats for
audiobooks and podcasts:
+ AAC (M4A, M4B, M4P) (up to 320 kbps)
+ MP3 (up to 320 kbps)
+ MP3 Variable Bit Rate (VBR)
+ WAV
+ AA (audible.com spoken word, formats 2, 3, and 4)
+ AIFF

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Shuffle showing large song list, but playing only 17 songs ?

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