ITunes tells me I cannot sync a smart playlist that references another playlist, but combining playlists is how I like to shuffle my music. I especially like creating individual playlists with "last played is not in the last" and "limit to" and then combining them. Do I need more cleverly designed rules, or is IMatch not for me? Advice?

I have certainly been disappointed that smart playlists won't live update on the Iphone, but at least I could still combine playlists into "superplaylists."

Imatch won't allow this, and by that I mean, these superplaylists sync to the Iphone through a direct sync (with IMatch turned off), but as soon as I turn Imatch on again, they disappear.

  • I use Smart Playlists during sync as well. AFAIK the message is more a warning saying that smart playlists won't update on the iPhone.
    – nohillside
    Nov 17, 2011 at 13:12

4 Answers 4


I think the best option you have is to recreate your super playlists as a single more complex playlist.

When you are editing a smart playlist you can option click the '+' button (turns into '...' while you are holding option) and this creates a subgroup that can a condition of it's own.

This playlist picks music based on rating and last played choosing higher rated tracks more often:

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One technique I used in some playlists was to put NSFW tracks in a playlist and then build other playlists to exclude NSFW tracks. Putting tracks in a playlist is an easy way to add additional information about them without having to edit the ID3 tags. That doesn't work with these more complex smart playlists.

You will have to put additional information like that into the ID3 fields. You can use the comments block for this, but I don't like to do that because I like to be able to add this kind of flag to multiple tracks at once and I can't do that as I may be losing comments already entered. Genre works if you're willing to use that instead. Any field will work; as I don't have tracks that use grouping I used that for my own NSFW tags.

One slightly more complex place to put these kinds of tags is the 'Category' field. iTunes keeps a category field but doesn't show that field in the editing UI so it's normally not used for anything. Doug's Applescripts offers a script that will let you edit this field. (script and instructions)

  • This technique is great for iTunes Match, but if you have another device you sync to that doesn't use iTunes Match, it might not end up ordering things properly (e.g. for an ordered by Last Played list). In order to get things in the right order for the non-Match device, I have to use another playlist to reference the list and limit it to x number of songs selected by least recently played.
    – alord1689
    Feb 2, 2012 at 22:08

Weird, but I have found a way to nest smartplaylists. If you try to add the other playlist as a criteria pressing the +, the list won't sync with iTunes Match. BUT if you just add the criteria pressing the "..." button it will (!)


I don't think this is possible at all. So when you're trying to combine normal playlists into "super playlists", you are out of luck. Note that, those playlists would still work, just not get synces via iTunes Match.

However, if you only try to combine smart playlists, you can always build more refined rules. Just add the the original rules to the newly created playlist. A somewhat hidden feature is that you can nest conditions to get more complex rules by holding the alt/option key clicking the + button.


It's more fundimental, from what I can tell. For some reason, there are certain tags (meta-data) associated with an iTunes track that DO sync, and some that DO NOT. To illustrate the scenario:

  1. I tag 11 songs with grouping XXX.
  2. I create a smart playlist with grouping XXX as the criteria. The list on the mac populates as expected. The list is created on the IOS device, but it's empty.
  3. I add a tag of YYY to the artist field on the same tracks
  4. I modify the smartlist filter to include the artist criteria of YYY. The list on the mac populates as expected. The list is persisted on the IOS device, but it's still empty.
  5. I remove the grouping criteria from my smartlist filter, leaving only the artist criteria of YYY. Suddenly, the list on the IOS device is populated as expected.

It took me about an hour with Apple Support to explain this bug, and in the end they agreed it was a bug. Any criteria that populates a smartlist should populate the IOS device through iTunes match.

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