On-the-Go Playlist doesn't work

When I create an on-the-go playlist on my ipod it refuses to play.
For example say I add two songs by holding down the center button on the scroll wheel then navigate to playlists. With the 'On-the-go' playlist highlighted I press Play and nothing happens.
If I go into the On-the-go playlist I can see the two songs I added however can only play the songs one at a time. The behaviour of my other playlists is fine ipod plays them ok and individual songs are shown as being 1 of X.
Any ideas ?
AMD +3000 Athlon 64 Windows XP Pro

Ok. If you find the song in a list (ie when you search by artist or album) and you hold down the center button, it works.
But, I want to put songs on my playlist when I hear them on random, when I cant highlight them without lots of work.
Let me know if you discover anything else...
iBook Mac OS 9.0.x

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