Update #3: I was playing around with my smart playlists this morning and discovered an additional tidbit of information that may be useful for some. When syncing smart playlists, pay attention to which column you have the ordered the music by.
As you can see in the above screenshot I have my playlist sorted by ‘Date Added’ which is exactly how I want things ordered. Once I synced my iPhone playlist showed my music sorted by ‘Date Added’ as well.
If I were to have ‘Play Count’ selected as the column to sort by and then synced my iPhone, then that playlist would display the songs ordered by ‘Play Count’
I found this out while playing with the Apple Remote app for the iPhone/iPod Touch. The selected column to sort by also effects how playlists are displayed in the iPhone Remote App.
Update #2: New updates that came out kinda fix this problem. Read more here.
I noticed the other day that Smart Playlists were not syncing correctly to both my wife and my own iPhone.
I found one fix that allowed the sort order to be correct, but disabled the Live updating function of the Smart Playlists. Which meant that every time an attribute of the playlist was updated (Such as rating a new song for my ’5 Stars’ playlist) nothing was updated upon syncing with my iPhone.
This totally defeats the purpose of a playlist that automagically updates my iPhone with the last 100 added, or top rated songs. ARGH!
Alas, after following a suggestion from this discussion thread (Thanks Dave Jelfs!) we now have a solution. In fact there’s even a bonus side effect for those who only want to sync music, and not video within your playlists.
Update: Joel S points out that this is not totally accurate. “In my own testing, these playlists will still include Music Videos.”
First find your Smart Playlist in the sidebar.
Ctrl + Click on the playlist and select “Edit Smart Playlist”
A new window will appear with all the settings for that particular playlist. Add a new rule of ‘Playlist is Music’
You’ll notice ‘Live updating’ is still on.
Now sync your playlist with your phone. TaDa!
While is is a workaround it does allow for the playlist to be synced, auto updated and appear sorted as you wish on the iPhone.
Like my previous troubleshooting articles I hope this post will be quickly updated when Apple roles out a fix. Until then, happy Smart Playlist syncing!
As with everything YMMV. I was using the following setup.
Macbook Pro 1.83 Ghz
Snow Leopard 10.6.1
iTunes 9.0.1
iPhone OS 3.1
If you have an improvement please leave a comment.



Fantastic! My smart playlists are now smart again… I never thought it possible – thanks.
You = genius!
Ok adding Music worked! I still say iTunes and apple to need to get it together. Annoying!!! I expect this from Windows not from Apple.
[..] A little unrelated, but I quite simply liked this webpage post [..]
Worked like a charm! Now my Smart Playlists show up on the iPhone. Thanks for the fix!
Thanks!
This has bothered me for so long. I’m eternally grateful.
Quite interesting, well I just wanted some songs and got your blog. Thanks for this one mate
I just loved it. An additional comment or feedback which I would like to give is that this theme is quite boring and you need to work on it but everything else I fine.
Hey,
Thanks, your tip is **STILL** needed — and yes it WORKED!!!!!!!!!!! Somehow despite having the latest iTunes 9.0.3 and iPhone OS 3.1.3 (iPod Touch 2G if it matters), not having this workaround DIDN’T work. Only after adding the “Playlist is Music” did it all work as expected!!!!!
THANKS!!!!!!!!!!
Finally. Problem solved. Thank you for posting this
Thank you!Thank you!Thank you!Thank you!Thank you!Thank you!Thank you!Thank you!Thank you!Thank you!Thank you!Thank you!Thank you!Thank you!
That was driving me NUTS!!!!!!!!!!!!
THANK YOU! THANK YOU! THANK YOU!
Hey all, I just updated this post. It looks like which column is sorted in iTunes before a sync is important for sorting the music on the iPhone!
Alas, the “Playlist is Music” workaround didn’t work on my iPod Touch running 3.1.3 with iTunes 9.0.3. Only disabling live updates seems to fix the “Top 25 Most Played”-is-random-songs bug.
Anyone know how to get to this work with Podcasts, playlist is music isn’t suitable.
THANKYOU
this has been bugging me for AGES, and my google fu failed me in finding an answer. I am not entirely happy that Apple have let this bug between itunes/iDevice synching last so long, but incredibly happy that you have found such an easy workaround !
thank you again !
It works! Finally! Thank you
Nice one — I’ve been banging my head against a wall on this issue for awhile. Great to have it fixed and have my smart playlists work as expected. Thanks for sharing!
thanks mate. you are a champion! was annoying the bejezes out of me and now it is fixed.
Thanks so much! Hated having to toggle “live updating”. Ditto on the wishes apple took care of this bug since it seems to have been around awhile…
It works!! Thank you very much!!
Helped!!! Many thanks.
… I don’t even know how to thank you… this was bringing me a discomfort the likes of which I could not put into words.
A huge “thank you” from Italy!
EXCELLENT, THANK YOU SO MUCH!!!! YOU DESERVE A PAT ON THE BACK:)
Kewl! Thanks.
Worked like a charm. Thanks!
Thank you so much, a fix at last. This has been driving me crazy.
Been searching for ages! Thank you it worked!