Dragging Playlists- some load to the ipod, others don't

I have a first gen ipod set for no autofill. I have a lot of playlists in my source list. For most of the playlists, if I drag them to the ipod shuffle entry, the green plus-sign shows up and they get loaded onto my ipod. But I have a new playlist, created from adding a new CD to my library, which will not load.
When I start to drag it up to my ipod's entry in the source list, the green plus sign shows up as it passes the other playlists, but when I get to the shuffle, there is no plus sign, and nothing gets added to my ipod.
What gives?

I have a first gen ipod set for no autofill. I have
a lot of playlists in my source list. For most of the
playlists, if I drag them to the ipod shuffle entry,
the green plus-sign shows up and they get loaded onto
my ipod. But I have a new playlist, created from
adding a new CD to my library, which will not load.
When I start to drag it up to my ipod's entry in the
source list, the green plus sign shows up as it
passes the other playlists, but when I get to the
shuffle, there is no plus sign, and nothing gets
added to my ipod.
What gives?
Possibly the tracks in that playlist are in a format/ecoding/bitrate that the Shuffle can't play... CHeck one of them by selecting it and clicking File>Get Info> Summary... let us know what it says.

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