If you're manually selecting playlists to sync (because your iPod is smaller than your music collection), have you selected Recently Added in iPod Preferences?

I'm not sure what you are trying to say about "selected Recently Added in iPod Preferences". Can you be more specific?

I do remember trying to right-click the playlist and manually updating it.

When you plug in your iPod, the iPod Preferences button appears at the bottom right of the iTunes window. Click it to see how iTunes is synchronizing with iPod. The window will give you the option of manually selecting playlists to sync, which is a good choice if your iPod is smaller than your music collection.

If the manual selection option is already chosen, then you'll probably find "Recently Added" hasn't been checked. If all of your music is supposed to be syncing, then I can't answer your question.

Of course, another think to check is the Recently Added playlist to confirm that songs have been added in the last two weeks. If you're not frequently adding new music, you might want to change the smart playlist to contain songs selected by "Most Recently Added."

I had this too.

Checked the date on my iPod and found that it had reset to Jan 2002. I guess this must have happened last time my iPod ran out of juice totally.

Change the date and time to match your computer and it should synch up again.

Wouldn't it be nice if Itunes could synch the time automatically for you on connection of your iPod.

I was pretty sure it did-

Oh that's probably it. The date on it was Jan 2000. I changed it but I need to charge it first and then I'll update the lists. I'm sure that's it though.

Thanks a ton!