Creative Media Source 5 and Zen

I own the Zen VW and use the Creative Media Source 5. The problem I find is when I try to transfer songs to the Zen. I am trying to copy my smart playlist of fi've star tracks over. On the pc it has over 000 tracks, but only 550 or so end up on my Zen, what can I do to make sure all the tracks transfer over?

What I have to do to make sure that every song gets transfered over, is to copy them in sets of 50 at a time. But with each set of 50, I dont get every song on the Zen, I have to delete how ever man of the 50 came over, and transfer the set of 50 again, the second time, every of the 50 songs transfers over. This is a pain when I have a play list of 000 songs. I have tried the whole list of 000 songs in one transfer, and I only get about half, and with a second transfer, I dont get much more.
What can fix this problem?

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