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YES! I can't believe I didn't try this earlier. This problem has been bugging me for months! Anyway, if anyone is having trouble with their smart playlist order since updating iTunes or to iOS 5, simply right click the playlist in iTunes, DUPLICATE, delete the old one, and make sure the new one is checked to sync. Voila, magically fixed!

Kudos to billynumo and captainjman.

Creating duplicate and deleting old playlist did not work for me. iPhone still shows playlist in reverse order.

I'd be curious though, if you add a new song to the playlist, such as a new one that shows at the top of the list, does it still sort correctly when resynced? I've seen other solutions that worked for me until the playlist was updated and then things were all whack again.
 
Holy crap, this issue finally seems to be fixed between my updates to iOS 5.1 & iTunes 10.6 today. I'm getting proper ordering on my iPhone 4S when viewing a smart playlist ordered by Date Added. This was one of the first things I checked.
 
I finally fixed it on my iPhone 4S running 5.0.1 a few weeks ago by wiping all of the music from my iPhone (including going in and manually deleting the music that was left after disabling music syncing in iTunes). When I turned it back on, the orders of the playlists were all correct.

Yesterday, it stopped working again. Installed iOS 5.1 today, and it didn't fix it. I'm about to wipe the music and re-sync it again. It's crazy annoying.
 
Wow, i can't believe we're all still having this problem! It's super annoying to have no ordering of things properly.

I wonder what we all have in common which is causing this issue?
 
Wow, i can't believe we're all still having this problem! It's super annoying to have no ordering of things properly.

I wonder what we all have in common which is causing this issue?

What type of playlist do you have and how is it being sorted in iTunes? And how does it actually appear to be sorted on your device?

At least for me, the longstanding issue with sorting was resolved either with iOS 5.1 and/or iTunes 10.6. I had a smart playlist for songs with greater than 0 stars, and sorted from newest to oldest. On my iPhone it would populate that playlist from oldest to newest, but now it's fixed.
 
What type of playlist do you have and how is it being sorted in iTunes? And how does it actually appear to be sorted on your device?

At least for me, the longstanding issue with sorting was resolved either with iOS 5.1 and/or iTunes 10.6. I had a smart playlist for songs with greater than 0 stars, and sorted from newest to oldest. On my iPhone it would populate that playlist from oldest to newest, but now it's fixed.

iOS 5.01. iphone 4s. Itunes 10.5 and 10.6 SmartPlaylists and normal playlists the sort orders are wrong (I order by date added). I tried the delete playlists and re-create and that didn't work after the first sync.
 
iOS 5.01. iphone 4s. Itunes 10.5 and 10.6 SmartPlaylists and normal playlists the sort orders are wrong (I order by date added). I tried the delete playlists and re-create and that didn't work after the first sync.

My suggestion would be to try upgrading your iPhone to 5.1. This, with the combination of iTunes 10.6, should hopefully resolve your issue like it did for me.
 
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