Shuffle Setting doesn't work after iPod update

Question

After I update my iPod software my shuffle setting seems to only work on about half of my music. Formerly, when I had the shuffle setting turned to Songs it worked on everything, but since the update when I go to certain Genres or Playlists instead of saying 1 of 237 and playing them at random, instead it says 1 of 1, or 1 of 5, and that's it.
I can work around it by going first to settings and turning the shuffl off, then playing my list, then going back and turning the shuffle on and then heading down to Now Playing.
Is there any way to get that setting working normally again?
ipod video   Windows XP  
ipod video   Windows XP  

Answer 1

I had the same issue and worked around it the same way you have (start playlist, then select shuffle songs). I don't know if this will apply to you, but here's what I discovered. I had some tracks set to Skip when Shuffling, in my mind thinking those songs would be skipped when I shuffled the entire library, but I didn't realize that it would also skip those songs if they are in a playlist and you are doing Settings, Shuffle, Songs. (As opposed to the setting that Shuffles the whole library.)
Example: I have a playlist of Celtic songs, which I want to skip when I shuffle my "main" music library. But when I play the Celtic Playlist, I don't like to hear it in the same order every single time. I like to switch it up. So I'd put Settings to Shuffle and select Songs. And on my Playlist, it would say 1 of 1, instead of 1 of 27.
Check it out. I thought it was worth bringing up since your situation sounds so similar to mine.
(By the way...I continue to use the "work around" as you mentioned, so that I can still Shuffle my "main" library, which I don't include Celtic in.)