iTunes 9 + Smart Playlist + Live Updating + iPhone = FAIL


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.

Screen shot 2009-09-27 at 8.11.22 PMCtrl + Click on the playlist and select “Edit Smart Playlist”

Screen shot 2009-09-27 at 8.27.49 PMA new window will appear with all the settings for that particular playlist. Add a new rule  of ‘Playlist is Music’

Screen shot 2009-09-27 at 8.11.39 PM
Click to view

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.

88 thoughts on “iTunes 9 + Smart Playlist + Live Updating + iPhone = FAIL”

  1. 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.

  2. 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.

  3. 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!!!!!

  4. 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!!!!!!!!!!!!

  5. 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!

  6. 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.


    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 !

  8. 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!

  9. 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…

  10. … 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.

  11. “Playlist is Music” method will not work when you are using the “Match ANY” filter method on the smart playlist because your filter will then allow ALL songs under each category. This is only a good resolution for using the “Match ALL” This is mereley an oversight on Apples programming – how the heck did they have it correct before the 9.0 update and even into the new version 10.0 I just downloaded – I thought they might have fixed this in the recent update – WTF is going on with Apple these days – way out of character for them to be having all of these issue lately.

  12. PS> Issue is that I have to turn off live updating just before I’m about to sync up the Itouch then everything will work. Apple has now made this a 2 step process in my scenario.

  13. I’m such a newbie when it comes to all this, thanks for taking the time to write this up, keep them coming! iTunes 9 + Smart Playlist + Live Updating + iPhone = FAIL Chris Koerner was a wonderful read.

  14. Full Marks for this one. Alas Apple has left it still around in version 10. Read a few other workrounds for this issue, but your solution was the simplest.

  15. This bug is still there as of June, 2011. Running latest iOS and iTunes – create a Smart Playlist and if you leave the live updating default checkbox, the playlist is empty on the phone.

    Come on Apple! I thought your mantra is, “It Just All Works”

  16. What happens if your library is too large to fit on your iOS device? If I check playlist is music the playlist is 5 times the size of the device.

    1. Daniel,
      If your playlist is too large, you could always use the smart filters to limit by the number of songs or the total size of the files within the playlist.

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