itunes 9 messed up my Playlist.

I have exactly the same problem (Top 100 though). 🙂 It has also messed up all my other smart playlists.

All my smart playlists are messed up on my iPhone 3GS too. They look fine in iTunes 9, but not on my iPhone. They WERE fine on my iPhone yesterday, before I upgrade to iTunes 9 and iPhone OS 3.1!

Same problem here, though i have noticed this issue on OS 3.0! I tried making new sets of smart playlists and removing ALL the music on my phone to adding several songs to the list... one of them used to work, but now they are just messed up! :/

EDIT
I think this issue is caused by the iPhone itself, not iTunes. Expanding the list by clicking, for example, "Owie's iPhone" under "Devices" and looking through the playlist you will see that they are all fine... so it means that iTunes has done it's job properly, but it's the iPod.app that messed it all up! 😟

Message was edited by: owie007

*EDIT 2*
There seems to be a temporary fix! right click on the Smart Playlist and click "Edit Smart PLaylist" then uncheck "Live updating"

It's not THE final fix, but it'll do for now i guess...

Message was edited by: owie007

Thanks for your temporary fix, Owie007. I'm dealing with the same problem, too. And that's pretty upsetting...! Do you think it's the iPhone OS 3.1 which is guilty?

no worries... yeah, i do think it's the OS... it seems to have been there for a while. i hope they fix it in the next update!
all we could do now is everytime we sync our devices we must uncheck Live updating, it's better than having to endure the messed up playlists! O_o

I'm having this issue on my iPod classic. I have a smart playlist for podcasts, the newest podcasts are at the top of the list, now they are all out of order 😟

I'm having the same problem with my 120g iPod classic. I have a smart playlist for my podcasts and it shows up in iTunes but not on my iPod. I hate getting my iPod out on the subway to skip to the next podcast. Bummer!

Another solution is to create a non-smart playlist that is sorted the way you want, and then erase it and drag the smart playlist over just before you sync. A PITA, but it does work. Not sure it is easier than turning off Live Updating each time or not.

Yeah I am experiencing this problem too. All my smart playlists are messed up. Hope they fix this soon.

noticed the problem a few days ago, just looked for an answer and found this... Thnx for the temp fix 🙂

Fixed in iTunes 9.0.2 for my classic 😀

iTunes 9.0.2 hasn't fixed this problem on my iPhone 3GS. Perhaps the problem is with the iPhone's OS, rather than iTunes.

Just tested this problem with iTunes 9.0.3 and it's still broken!