New Playlist/upgraded software

Per the prompt, I upgraded to the latest software for my ipod after connecting. Now I can't get my ipod to recognize a new playlist. It shows me the playlist is there, and after several attempts at copying a CD into it, the songs are finally there too, but it will not show up on my ipod. FYI - I had to play the songs in order for the software to acknowledge them. There is no "recently added" field to be found like normal. I've synced it a couple of times and even restarted my computer. No such luck. Any ideas? Thank you!

My recommendation is to reinstall Desktop Version  6.10.

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